Salt and solid forms of tabernanthalog

ABSTRACT

Disclosed herein are salt and solid forms of tabernanthalog. Disclosed solid forms may be a polymorph of tabernanthalog fumarate, and/or may have improved properties, such as improved physical, chemical and/or pharmacokinetic properties. Disclosed salts include pharmaceutically acceptable salts of tabernanthalog. Disclosed solid forms include free base and salt forms of tabernanthalog, including amorphous and crystalline forms of tabernanthalog, such as tabernanthalog free base or a salt thereof. Also disclosed are methods for making the salts and solid forms and methods for administering the same. The salt and solid forms of tabernanthalog and salts thereof are useful for treating neurological disease and/or a psychiatric disorder in a subject.

CROSS-REFERENCES TO RELATED APPLICATIONS

This application claims priority to U.S. Provisional Application No.63/280,514 filed Nov. 17, 2021, U.S. Provisional Application No.63/280,519 filed Nov. 17, 2021, U.S. Provisional Application No.63/310,981 filed Feb. 16, 2022, U.S. Provisional Application No.63/316,998 filed Mar. 5, 2022, and U.S. Provisional Application No.63/319,734 filed Mar. 14, 2022, which are incorporated herein byreference in their entirety to the full extent permitted by law.

FIELD OF THE INVENTION

The present disclosure relates to salt and solid forms of8-methoxy-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (commonlyknown as tabernanthalog), processes for their preparation and their usein the manufacture of a medicament for treating patients. The disclosureis also directed to pharmaceutical compositions containing at least onesalt or solid form of tabernanthalog and to the therapeutic and/orprophylactic use of such salt and solid forms and compositions.

SUMMARY

The present disclosure is directed to salt and solid forms oftabernanthalog. It is also directed to the crystalline (such assolvates, non-solvates, polymorphs, salts, and a cocrystals) oramorphous (such as solvates, non-solvates, salts, and amorphizedco-crystals) forms of the salt and solid forms of tabernanthalog.

Also disclosed are methods for making the salt and solid forms oftabernanthalog, as well as methods for using the same. In someembodiments, the solid form of tabernanthalog is a polymorph of the freebase form of tabernanthalog. In other embodiments, the form oftabernanthalog is a salt form, such as a pharmaceutically acceptablesalt. In salt embodiments of tabernanthalog, the salt may be provided ina solid form. Such solid forms of salts can be amorphous or crystalline.The solid form of tabernanthalog or a salt thereof may be a crystallinesolid. In some embodiments, the crystalline solid may be substantially asingle form, such as a polymorph form. In other embodiments, the solidform of tabernanthalog may be a solvate, such as a hydrate.

In some embodiments, the disclosed salt and solid forms oftabernanthalog have at least one desired property, or at least oneparticularly improved property compared to other forms oftabernanthalog, such as tabernanthalog free base, or compared to anamorphous form of tabernanthalog. In other embodiments, the at least onedesired property, or the at least one particularly improved property ofthe salt and solid forms of tabernanthalog disclosed herein may comprisea physical property, a chemical property, a pharmacokinetic property, ora combination thereof. In yet other embodiments, the at least onedesired property, or the at least one particularly improved propertycomprises a melting point, a glass transition temperature, flowability,thermal stability, mechanical stability, shelf life, stability againstpolymorphic transition, a hygroscopic property, solubility in waterand/or organic solvents, reactivity, compatibility with excipientsand/or delivery vehicles, bioavailability, absorption, distribution,metabolism, excretion, toxicity including cytotoxicity, dissolutionrate, half-life, or a combination thereof.

Also disclosed herein are pharmaceutical compositions comprising a saltor a solid form of tabernanthalog, and further optionally comprising atleast one pharmaceutically acceptable excipient.

A method for administering the salt or solid form of tabernanthalog isalso disclosed herein. In some embodiments, the method comprisesadministering to a subject an effective amount of a salt or solid formof tabernanthalog, or a pharmaceutical composition thereof. In someembodiments, the subject is suffering from a neurological disease or apsychiatric disorder, or both, such as a neurodegenerative disorder. Theneurological disorder or psychiatric disorder, or both, may comprisedepression, addiction, anxiety, or a post-traumatic stress disorder. Theneurological disorder or psychiatric disorder, or both, may comprisetreatment resistant depression, suicidal ideation, major depressivedisorder, bipolar disorder, schizophrenia, or substance use disorder. Insome embodiments, the neurological disorder or psychiatric disorder, orboth, comprises stroke, traumatic brain injury, or a combinationthereof.

In some embodiments, administering the salt or solid form oftabernanthalog, or a pharmaceutical composition thereof comprises oral,intravenous, parenteral, or topical administration. In certainembodiments, oral administration is used. In other embodiments, the saltor solid form of tabernanthalog, or a pharmaceutical composition isadministration by injection, inhalation, intraocular, intravaginal,intrarectal or transdermal routes.

In some embodiments, the tabernanthalog fumarate salt is crystallinepolymorphic salt of tabernanthalog with Pattern #1, Pattern #2a, Pattern#2b, Pattern #2c, Pattern #2d, Pattern #3, Pattern #4a, Pattern #4b,Pattern #5, Pattern #6a, Pattern #6b, Pattern #7, Pattern #8, Pattern#9, Pattern #10, Pattern #11, Pattern #12, Pattern #13, Pattern #14,Pattern #15, Pattern #16, Pattern #17, Pattern #18, Pattern #19, Pattern#20, Pattern #21, Pattern #22, or a mixture thereof.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals as shown in Table 155.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals as shown in Table 156.

In some embodiments, the tabernanthalog fumarate salt has an ¹H NMRspectra as provided in FIGS. 295 and 296 .

In some embodiments, the tabernanthalog fumarate salt has a TGA profileas provided in FIG. 299 .

In some embodiments, the TGA profile of the tabernanthalog fumarate saltshows a first TG event (−2.1% w/w).

In some embodiments, the tabernanthalog fumarate salt has a DSC profileas provided in FIG. 300 .

In some embodiments, the DSC profile of the tabernanthalog fumarate saltexhibits a bimodal transition corresponding to the melting of twodifferent crystal forms.

In some embodiments, the tabernanthalog fumarate salt has a DVS profileas provided in FIG. 301 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 5.1°2θ, 10.2°2θ, 27.2°2θ, 18.1°2θ, 9°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 5.1°2θ, 10.2°2θ, 27.2°2θ, 18.1°2θ, 9°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals as shown in Table 157.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by XRPD signals at 25.6°2θ,16.4°2θ, 17.1°2θ, 23°2θ, 9.1°2θ, 27.3°2θ, 15.7°2θ, 26.8°2θ, 18.1°2θ,20.7°2θ, 12.3°2θ, 25°2θ, 22.8°2θ, 21°2θ, 14.2°2θ, 24.7°2θ, 17.4°2θ,18.8°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by XRPD signals at 25.6°2θ,16.4°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by two or more, or three XRPDsignals as shown in Table 158.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by an ¹H NMR spectrum as depictedin FIG. 313 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by an XRPD profile as depicted inFIG. 3 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by a TGA profile as depicted inFIG. 315 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by a DSC profile as depicted inFIG. 316 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2b characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 24.6°2θ,18.1°2θ, 9.0°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ, and 17.0°2θ,(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2b characterized by XRPD signals at 25.5°2θ,16.3°2θ, 24.6°2θ, 18.1°2θ, 9.0°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ,and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2b characterized by two or more, or three XRPDsignals as shown in Table 159.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 22.3°2θ, 27.2°2θ, 9°2θ, 18.1°2θ, 26.8°2θ, and 17.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 27.2°2θ, 9°2θ, 18.1°2θ, 26.8°2θ, and17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by two or more, or three XRPDsignals as shown in Table 160.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.3°2θ, 16.2°2θ,25.2°2θ, 9.1°2θ, 22.1°2θ, 26°2θ, 26.8°2θ, 18.1°2θ, and 19.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by XRPD signals at 25.6°2θ,16.3°2θ, 16.2°2θ, 25.2°2θ, 9.1°2θ, 22.1°2θ, 26°2θ, 26.8°2θ, 18.1°2θ, and19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by two or more, or three XRPDsignals as shown in Table 161.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 16.6°2θ,20.1°2θ, 26.0°2θ, 22.2°2θ, 26.8°2θ, 16.8°2θ, 18.8°2θ, and9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 16.6°2θ, 20.1°2θ, 26.0°2θ, 22.2°2θ, 26.8°2θ, 16.8°2θ, 18.8°2θ,and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by two or more, or three XRPDsignals as shown in Table 162.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 8.2°2θ,11.3°2θ, 9.0°2θ, 23.8°2θ, 19.3°2θ, 17.1°2θ, 19.4°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by XRPD signals at 25.5°2θ,16.3°2θ, 8.2°2θ, 11.3°2θ, 9.0°2θ, 23.8°2θ, 19.3°2θ, 17.1°2θ, 19.4°2θ,and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by two or more, or three XRPDsignals as shown in Table 163.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.3°2θ, 8.2°2θ,9.1°2θ, 17.2°2θ, 18.1°2θ, 26.8°2θ, 15.7°2θ, 27.3°2θ, and21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by XRPD signals at 25.6°2θ,16.3°2θ, 8.2°2θ, 9.1°2θ, 17.2°2θ, 18.1°2θ, 26.8°2θ, 15.7°2θ, 27.3°2θ,and 21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by two or more, or three XRPDsignals as shown in Table 164.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 16.9°2θ, 21.4°2θ,23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ, 25.5°2θ, 22.5°2θ, and23.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by XRPD signals at 8.2°2θ, 16.9°2θ,21.4°2θ, 23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ, 25.5°2θ, 22.5°2θ, and23.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by two or more, or three XRPDsignals as shown in Table 181B.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, 26.2°2θ, 22.1°2θ, and 33.6°2θ(±0.2°2θ; +0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, 25.4°2θ, 19.3°2θ, 26.2°2θ, 22.1°2θ, 33.6°2θ, and13°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, and 20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals as shown in Table 166.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by an ¹H NMR spectrum as depictsin FIG. 344 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by an XRPD profile as depicts inFIG. 13 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by TGA profile as depicted in FIG.347 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by a DSC profile as depicted inFIG. 348 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6b characterized by two or more, or three XRPDsignals selected from the group consisting of 19.4°2θ, 16.5°2θ, 20.5°2θ,25.3°2θ, 26°2θ, 22°2θ, 12.9°2θ, 8.2°2θ, 33.4°2θ, and 37.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6b characterized by XRPD signals at 19.4°2θ,16.5°2θ, 20.5°2θ, 25.3°2θ, 26°2θ, 22°2θ, 12.9°2θ, 8.2°2θ, 33.4°2θ, and37.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6b characterized by two or more, or three XRPDsignals as shown in Table 167.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.4°2θ, 25.6°2θ, 15.9°2θ,7.2°2θ, 24.9°2θ, 19.4°2θ, 9.1°2θ, 21.3°2θ, 19.8°2θ, and 16.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by XRPD signals at 16.4°2θ,25.6°2θ, 15.9°2θ, 7.2°2θ, 24.9°2θ, 19.4°2θ, 9.1°2θ, 21.3°2θ, 19.8°2θ,and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by two or more, or three XRPDsignals as shown in Table 168.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #8 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 15.8°2θ,24.2°2θ, 20.5°2θ, 24.8°2θ, 18°2θ, 19°2θ, 7.6°2θ, and 9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #8 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 15.8°2θ, 24.2°2θ, 20.5°2θ, 24.8°2θ, 18°2θ, 19°2θ, 7.6°2θ, and9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #8 characterized by two or more, or three XRPDsignals as shown in Table 169.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by two or more, or three XRPDsignals selected from the group consisting of 15.9°2θ, 25.6°2θ, 24.7°2θ,16.4°2θ, 19.5°2θ, 21.9°2θ, 17.1°2θ, 8°2θ, 9.2°2θ, and 20.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by XRPD signals at 15.9°2θ,25.6°2θ, 24.7°2θ, 16.4°2θ, 19.5°2θ, 21.9°2θ, 17.1°2θ, 8°2θ, 9.2°2θ, and20.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by two or more, or three XRPDsignals as shown in Table 170.

In some embodiments, the tabernanthalog monofumaratefmonoumarate salt iscrystalline polymorphic Pattern #10 characterized by two or more, orthree XRPD signals selected from the group consisting of 25.5°2θ,16.9°2θ, 16.3°2θ, 21.3°2θ, 23.5°2θ, 8.2°2θ, 10.8°2θ, 23.4°2θ, 9.1°2θ,and 19.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #10 characterized by XRPD signals at 25.5°2θ,16.9°2θ, 16.3°2θ, 21.3°2θ, 23.5°2θ, 8.2°2θ, 10.8°2θ, 23.4°2θ, 9.1°2θ,and 19.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #10 characterized by two or more, or three XRPDsignals as shown in Table 171.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.1°2θ, 25.7°2θ, 16.4°2θ,21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 20.9°2θ, and 17.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by XRPD signals at 16.1°2θ,25.7°2θ, 16.4°2θ, 21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 20.9°2θ,and 17.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by two or more, or three XRPDsignals as shown in Table 172.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #12 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.3°2θ, 25.6°2θ, 21.6°2θ,20.3°2θ, 8.3°2θ, 9.1°2θ, 18.2°2θ, 23°2θ, 10.8°2θ, and 14.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #12 characterized by XRPD signals at 16.3°2θ,25.6°2θ, 21.6°2θ, 20.3°2θ, 8.3°2θ, 9.1°2θ, 18.2°2θ, 23°2θ, 10.8°2θ, and14.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #12 characterized by two or more, or three XRPDsignals as shown in Table 173.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16°2θ, 16.4°2θ,25.0°2θ, 19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, and 10.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by XRPD signals at 25.6°2θ, 16°2θ,16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, and10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by two or more, or three XRPDsignals as shown in Table 174.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, and17°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, and 17°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals as shown in Table 181D.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by an ¹H NMR spectrum as depictedin FIG. 377E.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by an XRPD profile as depicted inFIG. 377F.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by a TGA profile as depicted inFIG. 377I.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by a DSC profile as depicted inFIG. 377J.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.2°2θ, 17°2θ, 25.5°2θ,23.3°2θ, 21°2θ, 16.9°2θ, 19.9°2θ, 24.4°2θ, 8.4°2θ, and 25.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by XRPD signals at 16.2°2θ, 17°2θ,25.5°2θ, 23.3°2θ, 21°2θ, 16.9°2θ, 19.9°2θ, 24.4°2θ, 8.4°2θ, and25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by two or more, or three XRPDsignals as shown in Table 176.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, 17°2θ,24.4°2θ, 19.3°2θ, 9.1°2θ, 16.8°2θ, 9.6°2θ, 18.1°2θ, and 22.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by XRPD signals at 25.6°2θ,16.4°2θ, 17°2θ, 24.4°2θ, 19.3°2θ, 9.1°2θ, 16.8°2θ, 9.6°2θ, 18.1°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by two or more, or three XRPDsignals as shown in Table 177.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, 16.6°2θ,23.6°2θ, 21.7°2θ, 19.6°2θ, 26.9°2θ, 9.1°2θ, 22.4°2θ, and23.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by XRPD signals at 25.6°2θ,16.4°2θ, 16.6°2θ, 23.6°2θ, 21.7°2θ, 19.6°2θ, 26.9°2θ, 9.1°2θ, 22.4°2θ,and 23.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by two or more, or three XRPDsignals as shown in Table 178.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16°2θ, 18°2θ,16.3°2θ, 21.4°2θ, 26.8°2θ, 23°2θ, 25.9°2θ, 15.5°2θ, and 11°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by XRPD signals at 25.6°2θ, 16°2θ,18°2θ, 16.3°2θ, 21.4°2θ, 26.8°2θ, 23°2θ, 25.9°2θ, 15.5°2θ, and11°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by two or more, or three XRPDsignals as shown in Table 179.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 25.5°2θ, 16.4°2θ,20.5°2θ, 16.3°2θ, 26.7°2θ, 22.8°2θ, 19.5°2θ, 19.4°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by XRPD signals at 25.6°2θ,25.5°2θ, 16.4°2θ, 20.5°2θ, 16.3°2θ, 26.7°2θ, 22.8°2θ, 19.5°2θ, 19.4°2θ,and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by two or more, or three XRPDsignals as shown in Table 180.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #20 characterized by two or more, or three XRPDsignals selected from the group consisting of 6.1°2θ, 25.5°2θ, 16.3°2θ,19.0°2θ, 18.2°2θ, 15.9°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #20 characterized by XRPD signals at 6.1°2θ,25.5°2θ, 16.3°2θ, 19.0°2θ, 18.2°2θ, 15.9°2θ, and 16.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #20 characterized by two or more, or three XRPDsignals as shown in Table 181.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by two or more, or three XRPDsignals selected from the group consisting of 19.2°2θ, 16.7°2θ, 25.4°2θ,22.2°2θ, 27.2°2θ, 18.1°2θ, 17.7°2θ, 21.2°2θ, 26.1°2θ, and6.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by XRPD signals at 19.2°2θ,16.7°2θ, 25.4°2θ, 22.2°2θ, 27.2°2θ, 18.1°2θ, 17.7°2θ, 21.2°2θ, 26.1°2θ,and 6.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by two or more, or three XRPDsignals as shown in Table 182.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by two or more, or three XRPDsignals selected from the group consisting of 18.9°2θ, 19.3°2θ, 16.7°2θ,27.3°2θ, 18.2°2θ, 25.5°2θ, 6.7°2θ, 17.7°2θ, 20.2°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by XRPD signals at 18.9°2θ,19.3°2θ, 16.7°2θ, 27.3°2θ, 18.2°2θ, 25.5°2θ, 6.7°2θ, 17.7°2θ, 20.2°2θ,and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by two or more, or three XRPDsignals as shown in Table 183.

In some embodiments, the tabernanthalog monofumarate salt has Pattern#6a (Form A) has a crystal data as shown in FIG. 285 when collectedusing Single Crystal XRD.

In some embodiments, Form A of the tabernanthalog monofumarate salt isobtained from suspension equilibration of the tabernanthalog fumaratesalt in water (5 vol) at 90° C. and the product is isolated byfiltration and dried under sustained nitrogen flux (<1 bar) over 20 h at20° C.

In some embodiments, Form A of the tabernanthalog monofumarate salt isobtained from suspension equilibration of the tabernanthalog fumaratesalt in water (5 vol) at 20° C. and the product is isolated byfiltration and dried under sustained nitrogen flux (<1 bar) over 20 h at20° C.

In some embodiments, Form B of the tabernanthalog monofumarate salt isobtained from suspension equilibration of the tabernanthalog fumaratesalt in acetonitrile (5 vol) at 40° C. and the product is isolated bycentrifugation and oven-dried under vacuum over 20 h at 40° C.

In some embodiments, the tabernanthalog hemifumarate salt has Pattern#14 (Form I) has a crystal data as shown in FIG. 286 when collectedusing single Crystal XRD.

In some embodiments, Form I of the tabernanthalog hemifumarate salt isobtained from dissolution of Tabernanthalog (native); TBG Native andfumaric acid (0.5 equiv) in methanol (20 vol).

In some embodiments, the tabernanthalog fumarate salt Form A (unaryfumarate, Pattern #6a), is prepared from water (anhydrous form,generated via suspension equilibration in water at 20° C.).

In some embodiments, in the presence of Form A, Form B slowly evolvesinto Form A under competitive suspension equilibration conditions.

In some embodiments, metastable forms obtained via suspensionequilibration and wet pellets, readily undergo conversion into Form Aduring drying.

In some embodiments, Form A exhibits greatest relative stability amongstother forms of the tabernanthalog fumarate salt.

In some embodiments, the hemi-fumarate salt of the tabernanthalogfumarate salt is prepared and re-proportionated into the fumarate saltduring an ageing cycle.

In some embodiments, stability assessment of the supplied material(Pattern #1) at 40° C./75% RH executed over a 4-to-5-week period showsno evidence for hydrate formation, chemical degradation ordisproportionation of the API.

In some embodiments, the tabernanthalog salt is a tabernanthalog sorbatesalt, a tabernanthalog tartrate salt, a tabernanthalog maleate salt, ora tabernanthalog benzoate salt.

In some embodiments, the tabernanthalog salt has at least one of thefollowing characteristics: (a) a unique powder diffraction pattern byXRPD, (b) a flat baseline leading to single melt event by DSC, (c) aflat baseline up to the melt by TGA, (d) a significantly reducedimpurity burden and absence of trace solvents by ¹H NMR, and (e) anoptically crystalline and reasonably equant morphology undercross-polarized filter.

In yet other embodiments, the tabernanthalog salt is at least about 95%pure as measured by HPLC.

In other embodiments, the tabernanthalog salt is at least about 95% pureas measured by UV chromatographic method.

In some embodiments, Form A of the tabernanthalog sorbate salt isobtained from heat-up/cool-down crystallization of tabernanthalog(native) with sorbic acid in ethanol (5.0 vol) at 85° C. The product wasisolated by centrifugation and was oven-dried under reduced pressureover 20 h at 40° C.

In yet other embodiments, Form A of the tabernanthalog sorbate salt isobtained heat-up/cool-down crystallization of tabernanthalog (native)with sorbic acid in ethanol (3.0 vol) and the salt is isolated byfiltration and dried under sustained nitrogen flux (<1 bar) over 20 h at20° C.

In one embodiment, Form A of the tabernanthalog sorbate salt is a unarysorbate with 24.7% w/w th., sorbic acid (i.e., 1.0 mol of API to 1.0 molsorbic acid).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ,22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, and 21.4°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4° 20, and 24.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, Form A of the tabernanthalog sorbate salt iscrystalline characterized two or more, or three XRPD signals as shown inTable 216.

In some embodiments, Form A of the tabernanthalog sorbate salt iscrystalline characterized two or more, or three XRPD signals as shown inFIG. 384 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan ¹H NMR spectrum as depicted in FIG. 451 , FIG. 561 , or FIG. 562 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsa DSC profile as depicted in FIG. 453 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsa TGA profile as depicted in FIG. 454 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsa DVS profile as depicted in FIG. 455 or FIG. 456 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan XRPD pattern as depicted in FIG. 384 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan XRPD pattern post DVS as depicted in FIG. 458 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan HPLC spectrum as depicted in FIG. 460 or FIG. 566 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsat least one property as listed in Table 192.

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by XRPD signals at 5.7°2θ,11.4°2θ, and 22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by two or more, or three XRPDsignals selected from the group consisting of 5.7°2θ, 11.4°2θ, and22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by XRPD signals at 5.7°2θ,11.4°2θ, 22.6°2θ and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by two or more, or three XRPDsignals selected from the group consisting of 5.7°2θ, 11.4°2θ, 22.6°2θand 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt (Form A) has acrystal data when collected using Single Crystal XRD as follows:C₂₀H₂₆N₂O₃, M_(r)=342.43, monoclinic, P2_(1/c) (No. 14), a=9.3410(3)Å,b=6.4173(2)Å, c=30.5108(12)Å, b=95.374(3)°, a=g=90°, V=1820.90(11) Å³,T=100(2) K, Z=4, Z′=1, m(Cu K_(α))=0.675 mm⁻¹, 13832 reflectionsmeasured, 3694 unique (R_(int)=0.0462) which were used in allcalculations. The final wR₂ was 0.2098 (all data) and R_(I) was 0.0826(I≥2σ(I)).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form B; Pattern #1) and characterized by XRPD signals at7.5°2θ, and 15.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form C; Pattern #2) and characterized by XRPD signals at5.7°2θ, and 11.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form C; Pattern #2) and characterized by XRPD signals at5.7°2θ, 22.4°2θ, 11.5°2θ, 16.7°2θ, 17.3°2θ, 18.5°2θ, 18.7°2θ, 17.8°2θ,11.2°2θ, 20.1°2θ, 13.9°2θ, and 29.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form C; Pattern #2) and characterized by two or more, orthree XRPD signals selected from the group consisting of 5.7°2θ,22.4°2θ, 11.5°2θ, 16.7°2θ, 17.3°2θ, 18.5°2θ, 18.7°2θ, 17.8°2θ, 11.2°2θ,20.1°2θ, 13.9°2θ, and 29.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog sorbate salt·H₂O (hydrate) has acrystal data when collected using Single Crystal XRD as follows:C₂₀H₂₈N₂O₄, M_(r)=360.44, monoclinic, P2_(1/c) (No. 14),a=16.07470(10)Å, b=12.14150(10)Å, c=10.85080(10)Å, b=109.2390(10°),a=g=90°, V=1999.49(3) Å³, T=100(2) K, Z=4, Z′=1, m(Cu Kα)=0.676 mm⁻¹,51305 reflections measured, 3786 unique (R_(int)=0.0483) which were usedin all calculations. The final wR₂ was 0.0874 (all data) and R_(I) was0.0347 (I≥2σ(I)).

In one embodiment, the tabernanthalog sorbate salt is characterized byone of the following properties: (1) show minimal reduction in CP (from99.76% area to 99.70% area), (2) is highly soluble in the SIF buffers(apart from FaSSGF), (3) exhibits higher crystallographic quality thanthe tabernanthalog fumarate salt, (4) has better solvent and impurityrejection on scale-up.

The foregoing and other objects, features, and advantages of theinvention will become more apparent from the following detaileddescription, which proceeds with reference to the accompanying figures.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings, which are included to provide a furtherunderstanding of the present disclosure, are incorporated in andconstitute a part of this specification, illustrate aspects of thepresent disclosure and, together with the detailed description, serve toexplain the principles of the present disclosure. The patent orapplication file contains at least one drawing executed in color. Copiesof this patent or patent application publication with color drawing(s)will be provided by the Office upon request and payment of the necessaryfee.

FIG. 1 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #15. The XRPD signals observed inthis diffractogram are characterized in Table 176.

FIG. 2 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #5. The XRPD signals observed in thisdiffractogram are characterized in Table 181B.

FIG. 3 depicts an XRPD diffractogram of a sample isolated fromacetonitrile/heptanes (10 vol acetonitrile/5 vol heptanes stirred at 40°C.) comprising crystalline tabernanthalog fumarate of Pattern #2a. TheXRPD signals observed in this diffractogram are characterized in Table158.

FIG. 4 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #1 isolated from 2-MeTHF/heptanes (10vol 2-MeTHF/5 vol heptanes stirred at 40° C.). The XRPD signals observedin this diffractogram are characterized in Table 157.

FIG. 5 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog hemifumarate salt having XRPD Pattern #21. The XRPDsignals observed in this diffractogram are characterized in Table 182.

FIG. 6 depicts a proton NMR spectrum of tabernanthalog hemifumaratesalt.

FIG. 7 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog hemifumarate salt having Pattern #14. The XRPD signalsobserved in this diffractogram are characterized in Table 181D.

FIG. 8 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #2b. The XRPD signals observed inthis diffractogram are characterized in Table 159.

FIG. 9 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog monofumarate of Pattern #8. The XRPD signals observed inthis diffractogram are characterized in Table 169.

FIG. 10 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #4a. The XRPD signals observed inthis diffractogram are characterized in Table 163.

FIG. 11 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #4b. The XRPD signals observed inthis diffractogram are characterized in Table 164.

FIG. 12 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #3. The XRPD signals observed in thisdiffractogram are characterized in Table 162.

FIG. 13 depicts an XRPD diffractogram of a sample comprising crystallinetabernanthalog fumarate of Pattern #6a. The XRPD signals observed inthis diffractogram are characterized in Table 166.

FIG. 14 depicts XRPD diffractograms of a sample comprising crystallinetabernanthalog fumarate crystallized from water (top two traces)compared to an alternate crystalline form of tabernanthalog fumarate(bottom trace). The XRPD signals observed in the top two traces in thediffractogram are characterized in Table 160.

FIG. 15 depicts XRPD diffractograms of a sample comprising crystallinetabernanthalog fumarate crystallized from methanol (top two traces)compared to an alternate crystalline form of tabernanthalog fumarate(bottom trace). The XRPD signals observed in the top two traces in thediffractogram are characterized in Table 167.

FIG. 16 depicts the XRPD profile of 1-A1 (Experiment Reference 1-SampleReference A1) (wet pellet, Pattern #12).

FIG. 17 depicts the XRPD profile of 1-B1 (Experiment Reference 1-SampleReference B1) (wet pellet, Pattern #2a, Form B).

FIG. 18 depicts the XRPD profile of 1-C1 (Experiment Reference 1-SampleReference C1) (wet pellet, Pattern #15).

FIG. 19 depicts the XRPD profile of 1-D1 (Experiment Reference 1-SampleReference D1) (wet pellet, Pattern #1).

FIG. 20 depicts the XRPD profile of 1-E1 (Experiment Reference 1-SampleReference E1) (wet pellet, Pattern #1).

FIG. 21 depicts the XRPD profile of 1-G1 (Experiment Reference 1-SampleReference G1) (wet pellet, Pattern #5).

FIG. 22 depicts the XRPD profile of 1-H1 (Experiment Reference 1-SampleReference H1) (wet pellet, Pattern #9).

FIG. 23 depicts the XRPD profile of 1-I1(Experiment Reference 1-SampleReference I1) (wet pellet, Pattern #10).

FIG. 24 depicts the XRPD profile of 1-J1 (Experiment Reference 1-SampleReference J1) (wet pellet, Pattern #8).

FIG. 25 depicts the XRPD profile of 1-K1 (Experiment Reference 1-SampleReference K1) (wet pellet, Pattern #6b).

FIG. 26 depicts the XRPD profile of 1-L1 (Experiment Reference 1-SampleReference L1) (wet pellet, not assigned).

FIG. 27 depicts the XRPD profile of 1-M1 (Experiment Reference 1-SampleReference M1) (wet pellet, Pattern #7).

FIG. 28 depicts the XRPD profile of 1-N1 (Experiment Reference 1-SampleReference N1) (wet pellet, Pattern #11).

FIG. 29 depicts the XRPD profile of 1-O1 (Experiment Reference 1-SampleReference O1) (wet pellet, Pattern #1).

FIG. 30 depicts the XRPD profile of 1-P1 (Experiment Reference 1-SampleReference P1) (wet pellet, Pattern #2c).

FIG. 31 depicts the XRPD profile of 1-R1 (Experiment Reference 1-SampleReference R1) (wet pellet, Pattern #1).

FIG. 32 depicts the XRPD profile of 1-S1 (Experiment Reference 1-SampleReference S1) (wet pellet, Pattern #1).

FIG. 33 depicts the XRPD profile of 1-T1 (Experiment Reference 1-SampleReference T1) (wet pellet, Pattern #1).

FIG. 34 depicts the XRPD patterns that matched the tabernanthalogmonofumarate salt (Sample Reference 1, Pattern #1).

FIG. 35 depicts the XRPD patterns that are approximate match with thetabernanthalog monofumarate salt (Sample Reference 1, Pattern #1).

FIG. 36 depicts the XRPD patterns that exhibit differences compared tothe tabernanthalog monofumarate salt (Sample Reference 1, Pattern #1).

FIG. 37 depicts the ¹H NMR spectrum of 2-A8 (Experiment Reference2-Sample Reference A8) (t=5 w, open vial), spectrum was acquired inDMSO-d₆ and calibrated to the non-deuterated solvent residual at 2.50ppm.

FIG. 38 depicts the ¹H NMR spectrum of 2-B8 (Experiment Reference2-Sample Reference B8) (t=5 w, double bagged open vial), spectrum wasacquired in DMSO-d₆ and calibrated to the non-deuterated solventresidual at 2.50 ppm.

FIG. 39 depicts the TGA profile of 2-A8 (Experiment Reference 2-SampleReference A8) (t=5 weeks), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 40 depicts the TGA profile of 2-B8 (Experiment Reference 2-SampleReference B8) (t=5 weeks), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 41 depicts the DSC profile of 2-A8 (Experiment Reference 2-SampleReference A8) (t=5 weeks), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 42 depicts the DSC profile of 2-B8 (Experiment Reference 2-SampleReference B8) (t=5 weeks), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 43 depicts the XRPD profile of 2-A7 (Experiment Reference 2-SampleReference A7).

FIG. 44 depicts the XRPD profile of 2-A8 (Experiment Reference 2-SampleReference A8).

FIG. 45 depicts the XRPD profile of 2-B7 (Experiment Reference 2-SampleReference B7).

FIG. 46 depicts the XRPD profile of 2-B8 (Experiment Reference 2-SampleReference B8).

FIG. 47 depicts the HPLC profile of 2-A5 (Experiment Reference 2-SampleReference A5) (t=2 w).

FIG. 48 depicts the HPLC profile of 2-A6 (Experiment Reference 2-SampleReference A6) (t=3 w).

FIG. 49 depicts the HPLC profile of 2-A7 (Experiment Reference 2-SampleReference A7) (t=4 w).

FIG. 50 depicts the HPLC profile of 2-A8 (Experiment Reference 2-SampleReference A8) (t=5 w).

FIG. 51 depicts the HPLC profile of 2-B5 (Experiment Reference 2-SampleReference B5) (t=2 w).

FIG. 52 depicts the HPLC profile of 2-B6 (Experiment Reference 2-SampleReference B6) (t=3 w).

FIG. 53 depicts the HPLC profile of 2-B7 (Experiment Reference 2-SampleReference B7) (t=4 w).

FIG. 54 depicts the HPLC profile of 2-B8 (Experiment Reference 2-SampleReference B8) (t=5 w).

FIG. 55 depicts the 2-A (Experiment Reference 2-Sample Reference A) and2-B (Experiment Reference 2-Sample Reference B) (t=0 h). Input for bothis Pattern #1, Sample Reference 1 (ca. 100 mg). The photograph shows thevials right before being subjected to 75% RH.

FIG. 56 depicts the 2-A1 (Experiment Reference 2-Sample Reference A1)and 2-B1 (Experiment Reference 2-Sample Reference B1) (t=3 h).

FIG. 57 depicts the 2-A2 (Experiment Reference 2-Sample Reference A2)and 2-B2 (Experiment Reference 2-Sample Reference B2) (t=24 h).

FIG. 58 depicts the 2-A3 (Experiment Reference 2-Sample Reference A3)and 2-B3 (Experiment Reference 2-Sample Reference B3) (t=4 d).

FIG. 59 depicts the 2-A4 (Experiment Reference 2-Sample Reference A4)and 2-B4 (Experiment Reference 2-Sample Reference B4) (t=7 d).

FIG. 60 depicts the 2-A6 (Experiment Reference 2-Sample Reference A6)and 2-B6 (Experiment Reference 2-Sample Reference B6) (t=3 w).

FIG. 61 depicts the 2-A8 (Experiment Reference 2-Sample Reference A8)and 2-B8 (Experiment Reference 2-Sample Reference B8) (t=5 w).

FIG. 62 depicts the XRPD diffractogram overlay of the time pointmonitoring of 2-A (open vial) at 75% RH at 40° C. Overlay of, frombottom to top, the tabernanthalog monofumarate (Sample Reference 1,t=0), 2-A1 (t=3 h), 2-A2 (t=24 h), 2-A3 (t=48 h), 2-A4 (t=7 days), 2-A5(t=2 weeks), 2-A6 (t=3 weeks), 2-A7 (t=4 weeks), 2-A8 (t=5 weeks).

FIG. 63 depicts the XRPD diffractogram overlay of the time pointmonitoring of 2-B (double bagged open vial) at 75% RH at 40° C. Overlayof, from bottom to top, the tabernanthalog monofumarate salt (SampleReference 1, t=0), 2-B1 (t=3 h), 2-B2 (t=24 h), 2-B3 (t=48 h), 2-B4 (t=7days), 2-B5 (t=2 weeks), 2-B6 (t=3 weeks), 2-B7 (t=4 weeks), 2-B8 (t=5weeks).

FIG. 64 depicts the TGA overlay of 2-A8 (Experiment Reference 2-SampleReference A8) (t=5 weeks, open vial) and the tabernanthalog monofumaratesalt (Sample Reference 1, Pattern #1, t=0).

FIG. 65 depicts the TGA overlay of 2-B8 (Experiment Reference 2-SampleReference B8) (t=5 weeks, double-bagged vial) and the tabernanthalogmonofumarate salt (Sample Reference 1, Pattern #1, t=0).

FIG. 66 depicts the DSC overlay of 2-A8 (Experiment Reference 2-SampleReference A8) (bottom, t=5 weeks, open vial) and the tabernanthalogmonofumarate salt (Sample Reference 1, Pattern #1, top t=0).

FIG. 67 depicts the DSC overlay of 2-B8 (Experiment Reference 2-SampleReference B8) (t=5 weeks, double-bagged vial) and the tabernanthalogmonofumarate salt (Sample Reference 1, Pattern #1, t=0).

FIG. 68 depicts the DSC thermocycle of the tabernanthalog monofumaratesalt (Sample Reference 1, Pattern #1). Coordinate system: Normalized tosample size (Y-Axis), Reference temperature (X-Axis).

FIG. 69 depicts the DSC thermocycle of the tabernanthalog monofumaratesalt (Sample Reference 1, Pattern #1). Coordinate system: Normalized tosample size (Y-Axis), time (X-Axis).

FIG. 70 depicts the DSC of the tabernanthalog monofumarate salt (SampleReference 1, Pattern #1) that was acquired from 25° C. to 155° C. at aramp rate of +10° C./min.

FIG. 71 depicts the XRPD profile of the tabernanthalog monofumarate salt(Sample Reference 1, Pattern #1) specimen from DSC crucible at ca. 150°C.

FIG. 72 depicts the DSC thermocycle of the tabernanthalog monofumaratesalt (Sample Reference 1, Pattern #1).

FIG. 73 depicts the simultaneous DSC and TGA analyses of thetabernanthalog monofumarate salt (Sample Reference 1, Pattern #1).

FIG. 74 depicts the modulated DSC of the tabernanthalog monofumaratesalt (Sample Reference 1, Pattern #1).

FIG. 75 depicts the XRPD overlay of the tabernanthalog monofumarate salt(Sample Reference 1, Pattern #1, input, bottom) and specimen heated atca. 150° C. (top).

FIG. 76 depicts the DVS data of the tabernanthalog monofumarate salt(Sample Reference 1, Pattern #1).

FIG. 77 depicts the mass equilibrated DVS Data of the tabernanthalogmonofumarate salt (Sample Reference 1, Pattern #1). This is the massequilibrated DVS of the supplied material.

FIG. 78 depicts the mass equilibrated DVS data of 4-A4 (ExperimentReference 4-Sample Reference A4) (Form A, Pattern #6a).

FIG. 79 depicts the XRPD profile of Sample Reference 1 post DVS (Pattern#1, Mass equilibrated DVS) of the supplied material.

FIG. 80 depicts the XRPD overlay of the tabernanthalog monofumarate salt(Sample Reference 1, pattern #1, bottom) and post DVS (top, Pattern #1).

FIG. 81 depicts the XRPD profile of 4-A4 (Experiment Reference 4-SampleReference A4) post DVS (Pattern #6a) (Mass equilibrated DVS).

FIG. 82 depicts the DVS isotherm plot of the tabernanthalog monofumaratesalt (Sample Reference 1, pattern #1) obtained with 0% to 90% to 0% RHvs time.

FIG. 83 depicts the mass equilibrated DVS isotherm plot of thetabernanthalog monofumarate salt (Sample Reference 1, pattern #1)obtained with 0% to 90% to 0% RH.

FIG. 84 depicts the mass equilibrated DVS isotherm plot of thetabernanthalog monofumarate salt (4-A4, Pattern #6a, Form A) obtainedwith 0% to 90% to 0% RH.

FIG. 85 depicts the ¹H NMR spectrum of (5-01) (Experiment Reference5-Sample Reference 01) that was acquired in DMSO-d6 and calibrated tothe non-deuterated solvent residual at 2.50 ppm API to Fumaric acid, 1.0to 0.5.

FIG. 86 depicts the ¹H NMR spectrum of 5-B1 (Experiment Reference5-Sample Reference B1) that was acquired in DMSO-d6 and calibrated tothe non-deuterated solvent residual at 2.50 ppm API to Fumaric acid, 1.0to 0.5.

FIG. 86A depicts the ¹H NMR spectrum of 5-B3 was acquired in DMSO-d₆ andcalibrated to the non-deuterated solvent residual at 2.50 ppm API toFumaric acid, 1.0 to 0.5. Residual solvents: MeOH: 2.4% w/w, MeCN: 0.3%w/w (acetone detected derived from NMR tube, as it was not used in theprocess: 0.2% w/w).

FIG. 87 depicts the ¹H NMR spectrum of 5-B5 (Experiment Reference5-Sample Reference B5) that was acquired in DMSO-d6 and calibrated tothe non-deuterated solvent residual at 2.50 ppm API to Fumaric acid, 1.0to 0.5.

FIG. 87A depicts the DSC profile of 5-B3 (Experiment Reference 5-SampleReference B3), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 88 depicts the DSC profile of 5-B5 (Experiment Reference 5-SampleReference B5), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 89 depicts the XRPD profile of 5-B2 (Tabernanthalog·0.5 Fumarate;Experiment Reference 5-Sample Reference B2).

FIG. 89A depicts the XRPD profile of 5-B3 (Experiment Reference 5-SampleReference B3).

FIG. 90 depicts the XRPD profile of 5-B4 (Experiment Reference 5-SampleReference B4).

FIG. 91 depicts the XRPD profile of 5-B5 (Experiment Reference 5-SampleReference B5).

FIG. 92 depicts the LC-MS report of 5-O1 (Experiment Reference 5-SampleReference 01).

FIG. 93 relates to Experiment #1. It depicts the XRPD overlay of, fromtop to bottom, tabernanthalog (Native) (non-ionized,), tabernanthalogmonofumarate (Sample Reference 1, Pattern #1) and tabernanthaloghemifumarate (Pattern #14, 5-B2, and 5-B3,). Y-scale factor wasincreased for 5-B2 and -B3, as the intensity of their diffractograms waslow and difficult to compare with the reference powder diffractionpatterns.

FIG. 94 depicts the XRPD overlay of, form top to bottom, a mixture ofTabernanthalog·0.5 Fumarate and Tabernanthalog·Fumarate equilibrated inacetonitrile at 20° C., a mixture of Tabernanthalog·0.5 Fumarate andTabernanthalog·Fumarate equilibrated in acetonitrile at 40° C. andTabernanthalog fumarate Pattern 19.

FIG. 95 depicts the XRPD profile of 6-A2 (Experiment Reference 6-SampleReference A2) (Pattern #2b).

FIG. 96 depicts the XRPD profile of 6-B1 (Experiment Reference 6-SampleReference B1) (Pattern #1).

FIG. 97 depicts the XRPD profile of 6-B2 (Experiment Reference 6-SampleReference B2) (Pattern #1).

FIG. 98 depicts the XRPD profile of 6-C1 (Experiment Reference 6-SampleReference C1) (Pattern #1).

FIG. 99 depicts the XRPD profile of 6-C2 (Experiment Reference 6-SampleReference C2) (Pattern #1).

FIG. 100 depicts the XRPD profile of 6-D1 (Experiment Reference 6-SampleReference D1) (Pattern #3).

FIG. 101 depicts the XRPD profile of 6-D2 (Experiment Reference 6-SampleReference D2) (Pattern #3).

FIG. 102 depicts the XRPD profile of 6-E1 (Experiment Reference 6-SampleReference E1) (Pattern #4b).

FIG. 103 depicts the XRPD profile of 6-E2 (Experiment Reference 6-SampleReference E2) (Pattern #4b).

FIG. 104 depicts the XRPD profile of 6-F1 (Experiment Reference 6-SampleReference F1) (Pattern #5).

FIG. 105 depicts the XRPD profile of 6-F2 (Experiment Reference 6-SampleReference F2) (Pattern #4a).

FIG. 106 depicts the XRPD profile of 6-H1 (Experiment Reference 6-SampleReference H1) (Pattern #2d).

FIG. 107 depicts the XRPD profile of 6-H2 (Experiment Reference 6-SampleReference H2) (Pattern #2b).

FIG. 108 depicts the XRPD profile of 6-I1(Experiment Reference 6-SampleReference I1) (Pattern #1).

FIG. 109 depicts the XRPD profile of 6-I2 (Experiment Reference 6-SampleReference 12) (Pattern #1).

FIG. 110 depicts the XRPD profile of 6-J1 (Experiment Reference 6-SampleReference J1) (Pattern #8).

FIG. 111 depicts the XRPD profile of 6-K1 (Experiment Reference 6-SampleReference K1) (Pattern #4a).

FIG. 112 depicts the XRPD profile of 6-L1 (Experiment Reference 6-SampleReference L1) (Pattern #13).

FIG. 113 depicts the XRPD profile of 6-L2 (Experiment Reference 6-SampleReference L2) (Pattern #2b).

FIG. 114 depicts the XRPD profile of 6-M1 (Experiment Reference 6-SampleReference M1) (Pattern #1).

FIG. 115 depicts the XRPD profile of 6-M2 (Experiment Reference 6-SampleReference M2) (Pattern #1).

FIG. 116 depicts the XRPD profile of 6-N2 (Experiment Reference 6-SampleReference N2) (Pattern #1).

FIG. 117 depicts the XRPD profile of 6-01 (Experiment Reference 6-SampleReference 01) (Pattern #1).

FIG. 118 depicts the XRPD profile of 6-P2 (Experiment Reference 6-SampleReference P2) (Pattern #4a).

FIG. 119 depicts the XRPD profile of 6-Q2 (Experiment Reference 6-SampleReference Q2) (Pattern #2b).

FIG. 120 depicts the XRPD profile of 6-R1 (Experiment Reference 6-SampleReference R1) (Pattern #3).

FIG. 121 depicts the XRPD profile of 6-S1 (Experiment Reference 6-SampleReference S1) (Pattern #6a).

FIG. 122 depicts the XRPD profile of 7-A2 (Experiment Reference 7-SampleReference A2) (Pattern #19).

FIG. 123 depicts the XRPD profile of 7-B1 (Experiment Reference 7-SampleReference B1) (Pattern #2a).

FIG. 124 depicts the XRPD profile of 7-C1 (Experiment Reference 7-SampleReference C1) (Pattern #1).

FIG. 125 depicts the XRPD profile of 7-C2 (Experiment Reference 7-SampleReference C2) (Pattern #1).

FIG. 126 depicts the XRPD profile of 7-D1 (Experiment Reference 7-SampleReference D1) (Pattern #3).

FIG. 127 depicts the XRPD profile of 7-D2 (Experiment Reference 7-SampleReference D2) (Pattern #1).

FIG. 128 depicts the XRPD profile of 7-E2 (Experiment Reference 7-SampleReference E2) (Pattern #1).

FIG. 129 depicts the XRPD profile of 7-F1 (Experiment Reference 7-SampleReference F1) (Pattern #5).

FIG. 130 depicts the XRPD profile of 7-G1 (Experiment Reference 7-SampleReference G1) (Pattern #9).

FIG. 131 depicts the XRPD profile of 7-G2 (Experiment Reference 7-SampleReference G2) (Pattern #1).

FIG. 132 depicts the XRPD profile of 7-H2 (Experiment Reference 7-SampleReference H2) (Pattern #2b).

FIG. 133 depicts the XRPD profile of 7-I1(Experiment Reference 7-SampleReference I1) (Pattern #1).

FIG. 134 depicts the XRPD profile of 7-I2 (Experiment Reference 7-SampleReference 12) (Pattern #1).

FIG. 135 depicts the XRPD profile of 7-J1 (Experiment Reference 7-SampleReference J1) (Pattern #2a).

FIG. 136 depicts the XRPD profile of 7-J2 (Experiment Reference 7-SampleReference J2) (Pattern #2a).

FIG. 137 depicts the XRPD profile of 7-L2 (Experiment Reference 7-SampleReference L2) (Pattern #1).

FIG. 138 depicts the XRPD profile of 7-M1 (Experiment Reference 7-SampleReference M1) (Pattern #2a).

FIG. 139 depicts the XRPD profile of 7-M2 (Experiment Reference 7-SampleReference M2) (Pattern #2a).

FIG. 140 depicts the XRPD profile of 7-N1 (Experiment Reference 7-SampleReference N1) (Pattern #7).

FIG. 141 depicts the XRPD profile of 7-02 (Experiment Reference 7-SampleReference O2) (Pattern #2a).

FIG. 142 depicts the XRPD profile of 7-P1 (Experiment Reference 7-SampleReference P1) (Pattern #10).

FIG. 143 depicts the XRPD profile of 7-Q1 (Experiment Reference 7-SampleReference Q1) (Pattern #11).

FIG. 144 depicts the XRPD profile of 7-R1 (Experiment Reference 7-SampleReference R1) (Pattern #1).

FIG. 145 depicts the XRPD profile of 7-S1 (Experiment Reference 7-SampleReference S1) (Pattern #8, amorphized).

FIG. 146 depicts the ¹H NMR spectrum of 8-A4 (Experiment Reference8-Sample Reference A4), analysis was acquired in DMSO-d6 and calibratedto the non-deuterated solvent residual at 2.50 ppm API to Fumaric acid,1.0 to 1.0.

FIG. 147 depicts the ¹H NMR spectra overlay of 8-A4 (ExperimentReference 8-Sample Reference A4) and input (Sample Reference 1).

FIG. 148 depicts the TGA profile of 8-A4 (Experiment Reference 8-SampleReference A4), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 149 depicts the DSC profile of 8-A4 (Experiment Reference 8-SampleReference A4), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 150 depicts the XRPD profile of 8-A4 (Experiment Reference 8-SampleReference A4) (Form A, Pattern #6a).

FIG. 151 depicts the HPLC profile of 8-A4 (Experiment Reference 8-SampleReference A4) (Form A, Pattern #6a). The peak at ca. 2 min correspond toDMSO, as it was used as the sample diluent.

FIG. 152 depicts the PLM of 8-A4 (Experiment Reference 8-SampleReference A4) normal polarized (magnification×2).

FIG. 153 depicts the PLM of 8-A4 (Experiment Reference 8-SampleReference A4) cross polarized (magnification×2).

FIG. 154 depicts the PLM of 8-A4 (Experiment Reference 8-SampleReference A4) normal polarized (magnification×5).

FIG. 155 depicts the PLM of 8-A4 (Experiment Reference 8-SampleReference A4) normal polarized (magnification×5).

FIG. 156 depicts the monitoring the conversion of the tabernanthalogmonofumarate salt (Sample Reference1) in water at 20° C. by XRPDanalysis. Overlay of, from bottom to top, the tabernanthalogmonofumarate salt (Pattern #1, Sample Reference 1), 8-A1 (t=24 h), 8-A2(t=48 h), 8-A3 (t=4 d) and 8-A4 (t=10 d) wherein 8-A1=(ExperimentReference 8-Sample Reference A1); 8-A2=(Experiment Reference 8-SampleReference A2); 8-A3=(Experiment Reference 8-Sample Reference A3); and8-A4=(Experiment Reference 8-Sample Reference A4).

FIG. 157 depicts the XRPD diffractogram overlay of 8-A4 (ExperimentReference 8-Sample Reference A4) and 6-S2 (Experiment Reference 6-SampleReference S2).

FIG. 158 depicts the ¹H NMR spectrum of 9-A2 (Experiment Reference9-Sample Reference A2) that was acquired in DMSO-d₆ and calibrated tothe non-deuterated solvent residual at 2.50 ppm.

FIG. 159 depicts the ¹H NMR spectrum of 9-B2 (Experiment Reference9-Sample Reference B2), analysis was acquired in DMSO-d₆ and calibratedto the non-deuterated solvent residual at 2.50 ppm. Residual tBME 0.3%w/w.

FIG. 160 depicts the ¹H NMR spectrum of 9-C2 (Experiment Reference9-Sample Reference C2), analysis was acquired in DMSO-d₆ and calibratedto the non-deuterated solvent residual at 2.50 ppm. Residual IPAC 13.2%w/w (ca. th. solvate 22.8% w/w).

FIG. 161 depicts the ¹H NMR spectrum of 9-D2 (Experiment Reference9-Sample Reference D2), analysis was acquired in DMSO-d₆ and calibratedto the non-deuterated solvent residual at 2.50 ppm. Residual toluene6.0% w/w (ca. th. solvate 21.0% w/w).

FIG. 162 depicts the ¹H NMR spectrum of 9-E2 (Experiment Reference9-Sample Reference E2), analysis was acquired in DMSO-d₆ and calibratedto the non-deuterated solvent residual at 2.50 ppm.

FIG. 163 depicts the ¹H NMR spectrum of 9-F2 (Experiment Reference9-Sample Reference F2), analysis was acquired in DMSO-d₆ and calibratedto the non-deuterated solvent residual at 2.50 ppm.

FIG. 164 depicts the TGA profile of 9-A2 (Experiment Reference 9-SampleReference A2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 165 depicts the TGA profile of 9-B2 (Experiment Reference 9-SampleReference B2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 166 depicts the TGA profile of 9-C2 (Experiment Reference 9-SampleReference C2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 167 depicts the TGA profile of 9-D2 (Experiment Reference 9-SampleReference D2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 168 depicts the TGA profile of 9-E2 (Experiment Reference 9-SampleReference E2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 169 depicts the TGA profile of 9-F2 (Experiment Reference 9-SampleReference F2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 170 depicts the DSC profile of 9-A2 (Experiment Reference 9-SampleReference A2), analysis was acquired at a ramp rate of +10° C./minute.Higher melt event>200° C., was observed.

FIG. 171 depicts the DSC profile of 9-B2 (Experiment Reference 9-SampleReference B2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 172 depicts the DSC profile of 9-C2 (Experiment Reference 9-SampleReference C2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 173 depicts the DSC profile of 9-D2 (Experiment Reference 9-SampleReference D2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 174 depicts the DSC profile of 9-E2 (Experiment Reference 9-SampleReference E2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 175 depicts the DSC profile of 9-F2 (Experiment Reference 9-SampleReference F2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 176 depicts the DSC profile of 9-G2 (Experiment Reference 9-SampleReference G2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 177 depicts the XRPD profile of 9-A1 (Experiment Reference 9-SampleReference A1) (Incoherent).

FIG. 178 depicts the XRPD profile of 9-A2 (Experiment Reference 9-SampleReference A2) (Pattern #2c).

FIG. 179 depicts the XRPD profile of 9-B1 (Experiment Reference 9-SampleReference B1) (Pattern #1).

FIG. 180 depicts the XRPD profile of 9-B2 (Experiment Reference 9-SampleReference B2) (Pattern #1).

FIG. 181 depicts the XRPD profile of 9-C1 (Experiment Reference 9-SampleReference C1) (Pattern #8).

FIG. 182 depicts the XRPD profile of 9-C2 (Experiment Reference 9-SampleReference C2) (Pattern #8).

FIG. 183 depicts the XRPD profile of 9-D1 (Experiment Reference 9-SampleReference D1) (Pattern #3).

FIG. 184 depicts the XRPD profile of 9-D2 (Experiment Reference 9-SampleReference D2) (Pattern #3).

FIG. 185 depicts the XRPD profile of 9-E1 (Experiment Reference 9-SampleReference E1) (Pattern #2c).

FIG. 186 depicts the XRPD profile of 9-E2 (Experiment Reference 9-SampleReference E2) (Pattern #2c).

FIG. 187 depicts the XRPD profile of 9-F1 (Experiment Reference 9-SampleReference F1) (Pattern #2c).

FIG. 188 depicts the XRPD profile of 9-F2 (Experiment Reference 9-SampleReference F2) (Pattern #2c).

FIG. 189 depicts the XRPD profile of 9-G1 (Experiment Reference 9-SampleReference G1) (Pattern #2c).

FIG. 190 depicts the XRPD profile of 9-G2 (Experiment Reference 9-SampleReference G2) (Pattern #2c).

FIG. 191 depicts the 9-E2 (Experiment Reference 9-Sample Reference E2)cross polarized (magnification×2).

FIG. 192 depicts the 9-E2 (Experiment Reference 9-Sample Reference E2)normal polarized (magnification×5).

FIG. 193 depicts the 9-E2 (Experiment Reference 9-Sample Reference E2)cross polarized (magnification×5).

FIG. 194 depicts the 9-E2 (Experiment Reference 9-Sample Reference E2)normal polarized (magnification×25).

FIG. 195 depicts the 9-F2 (Experiment Reference 9-Sample Reference F2)normal polarized (magnification×2).

FIG. 196 depicts the 9-F2 (Experiment Reference 9-Sample Reference F2)normal polarized (magnification×5).

FIG. 197 depicts the 9-F2 (Experiment Reference 9-Sample Reference F2)cross polarized (magnification×5).

FIG. 198 depicts the 9-F2 (Experiment Reference 9-Sample Reference F2)normal polarized (magnification×25).

FIG. 199 depicts the XRPD diffractogram overlay of 9-A1 (ExperimentReference 9-Sample Reference A1) and 9-A2 (Experiment Reference 9-SampleReference A2) (water).

FIG. 200 depicts the XRPD diffractogram overlay of 9-B1 (ExperimentReference 9-Sample Reference B1) and 9-B2 (Experiment Reference 9-SampleReference B2) (tBME).

FIG. 201 depicts the XRPD diffractogram overlay of 9-C1 (ExperimentReference 9-Sample Reference C1) and 9-C2 (Experiment Reference 9-SampleReference C2) (iPAC).

FIG. 202 depicts the XRPD diffractogram overlay of 9-D1 (ExperimentReference 9-Sample Reference D1) and 9-D2 (Experiment Reference 9-SampleReference D2) (toluene).

FIG. 203 depicts the XRPD diffractogram overlay of 9-E1 (ExperimentReference 9-Sample Reference E1) and 9-E2 (Experiment Reference 9-SampleReference E2) (water).

FIG. 204 depicts the XRPD diffractogram overlay of 9-F1 (ExperimentReference 9-Sample Reference F1) and 9-F2 (Experiment Reference 9-SampleReference F2) (water).

FIG. 205 depicts the XRPD diffractogram overlay of 9-A2 (ExperimentReference 9-Sample Reference A2), 9-E2 (Experiment Reference 9-SampleReference E2) and 9-F2 (Experiment Reference 9-Sample Reference F2).

FIG. 206 depicts the XRPD diffractogram overlay of 8-A2 (ExperimentReference 8-Sample Reference A2) (input) and 9-F2 (Experiment Reference9-Sample Reference F2).

FIG. 207 depicts the DSC profile of 10-A1 (Experiment Reference10-Sample Reference A1), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 208 depicts the DSC profile of 10-B1 (Experiment Reference10-Sample Reference B1), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 209 depicts the XRPD profile of 10-A1 (Experiment Reference10-Sample Reference A1) (Pattern #22).

FIG. 210 depicts the DSC thermogram overlay of 9-E2 (ExperimentReference 9-Sample Reference E2) (red) and 10-B1 (Experiment Reference10-Sample Reference B1) (black).

FIG. 211 depicts the XRPD profile of 11-A2 (Experiment Reference11-Sample Reference A2) (Pattern #6a).

FIG. 212 depicts the XRPD profile of 11-B2 (Experiment Reference11-Sample Reference B2) (Pattern #6a).

FIG. 213 depicts the XRPD profile of 11-C2 (Experiment Reference11-Sample Reference C2) (Pattern #6a).

FIG. 214 depicts the XRPD profile of 11-D2 (Experiment Reference11-Sample Reference D2) (Pattern #5).

FIG. 215 depicts the XRPD profile of 11-E2 (Experiment Reference11-Sample Reference E2) (Pattern #6b).

FIG. 216 depicts the XRPD profile of 11-F2 (Experiment Reference11-Sample Reference F2) (Pattern #6a).

FIG. 217 depicts the XRPD profile of 11-G2 (Experiment Reference11-Sample Reference G2) (Pattern #1).

FIG. 218 depicts the XRPD profile of 11-H2 (Experiment Reference11-Sample Reference H2) (Pattern #6a).

FIG. 219 depicts the XRPD profile of 11-I2 (Experiment Reference11-Sample Reference 12) (Pattern #6b).

FIG. 220 depicts the XRPD profile of 11-J2 (Experiment Reference11-Sample Reference J2) (Pattern #6a).

FIG. 221 depicts the XRPD profile of 11-K2 (Experiment Reference11-Sample Reference K2) (Pattern #5).

FIG. 222 depicts the XRPD profile of 11-L2 (Experiment Reference11-Sample Reference L2) (Pattern #6a).

FIG. 223 depicts the XRPD profile of 11-M2 (Experiment Reference11-Sample Reference M2) (Pattern #6a).

FIG. 224 depicts the XRPD profile of 11-N2 (Experiment Reference11-Sample Reference N2) (Pattern #6a).

FIG. 225 depicts the XRPD profile of 11-02 (Experiment Reference11-Sample Reference 02) (Pattern #6a).

FIG. 226 depicts the XRPD profile of 11-P2 (Experiment Reference11-Sample Reference P2) (Pattern #5).

FIG. 227 depicts the XRPD profile of 11-Q2 (Experiment Reference11-Sample Reference Q2) (Pattern #14).

FIG. 228 depicts the DSC profile of 12-A1 (Experiment Reference12-Sample Reference A1), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 229 depicts the DSC profile of 12-B1 (Experiment Reference12-Sample Reference B1), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 230 depicts the XRPD profile of 12-A1 (Experiment Reference12-Sample Reference A1) (slow conversion to Pattern #6a).

FIG. 231 depicts the XRPD profile of 12-B1 (Experiment Reference12-Sample Reference B1) (slow conversion to Pattern #6a).

FIG. 232 depicts the DSC thermograms under neat grinding (NG, 12-A1(Experiment Reference 12-Sample Reference A1)) and under liquid assistedgrinding conditions (LAG, 12-B1 (Experiment Reference 12-SampleReference B1)). Tabernanthalog monofumarate (left, top and bottom,Pattern #1) 12-A1 (top right, NG, Pattern #6a), 12-B1 (bottom right,LAG, Pattern #6a).

FIG. 233 depicts the XRPD diffractograms under neat grinding (NG, 12-A1(Experiment Reference 12-Sample Reference A1), Pattern #6a, top right)and under liquid assisted grinding conditions (LAG, 12-B1 (ExperimentReference 12-Sample Reference B1), Pattern #6a, bottom, right). Inputmaterial (tabernanthalog monofumarate (left, top and bottom, Pattern#1).

FIG. 234 depicts the ¹H NMR spectrum of 13-B2 (Experiment Reference13-Sample Reference B2), analysis was acquired in MeOD-d₄ and calibratedto the non-deuterated solvent residual at 3.31 ppm. Residual DMSO 1.1%w/w (ca. th. solvate 18.4% w/w).

FIG. 235 depicts the ¹H NMR spectrum of 13-C2 (Experiment Reference13-Sample Reference C2), analysis was acquired in MeOD-d₄ and calibratedto the non-deuterated solvent residual at 3.31 ppm. Residual DMSO 0.6%w/w (ca. th. solvate 18.4% w/w).

FIG. 236 depicts the TGA profile of 13-B2 (Experiment Reference13-Sample Reference B2), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 237 depicts the TGA profile of 13-C2 (Experiment Reference13-Sample Reference C2), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 238 depicts the DSC profile of 13-B2 (Experiment Reference13-Sample Reference B2).

FIG. 239 depicts the DSC profile of 13-C2 (Experiment Reference13-Sample Reference C2).

FIG. 240 depicts the XRPD profile of 13-B1 (Experiment Reference13-Sample Reference B1) (wet sample, Pattern #24).

FIG. 241 depicts the XRPD profile of 13-B2 (Experiment Reference13-Sample Reference B2) (oven dried, Pattern #24).

FIG. 242 depicts the XRPD profile of 13-C1 (Experiment Reference13-Sample Reference C1) (wet sample, Pattern #23).

FIG. 243 depicts the XRPD profile of 13-C2 (Experiment Reference13-Sample Reference C2) (oven dried, Pattern #23).

FIG. 244 depicts the 13-B2 (Experiment Reference 13-Sample Reference B2)normal polarized (magnification×5).

FIG. 245 depicts the 13-B2 (Experiment Reference 13-Sample Reference B2)cross polarized (magnification×5).

FIG. 246 depicts the 13-B2 (Experiment Reference 13-Sample Reference B2)normal polarized (magnification×25).

FIG. 247 depicts the 13-C2 (Experiment Reference 13-Sample Reference C2)normal polarized (magnification×5).

FIG. 248 depicts the illustration of vapor diffusion experimentapparatus set-up.

FIG. 249 depicts the ¹H NMR spectrum of 14-A2 (Experiment Reference14-Sample Reference A2), analysis was acquired in MeOD-d₄ and calibratedto the non-deuterated solvent residual at 3.31 ppm. Residual DMSO 0.8%w/w (ca. th. solvate 18.4% w/w).

FIG. 250 depicts the ¹H NMR spectrum of 14-B2 (Experiment Reference14-Sample Reference B2), analysis was acquired in MeOD-d₄ and calibratedto the non-deuterated solvent residual at 3.31 ppm. Residual DMSO 0.9%w/w (ca. th. solvate 18.4% w/w).

FIG. 251 depicts the ¹H NMR spectrum of 14-C2 (Experiment Reference14-Sample Reference C2), analysis was acquired in MeOD-d₄ and calibratedto the non-deuterated solvent residual at 3.31 ppm. Residual DMSO 0.9%w/w (ca. th. solvate 18.4% w/w).

FIG. 252 depicts the TGA profile of 14-A2 (Experiment Reference14-Sample Reference A2), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 253 depicts the TGA profile of 14-B2 (Experiment Reference14-Sample Reference B2), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 254 depicts the TGA profile of 14-C2 (Experiment Reference14-Sample Reference C2), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 255 depicts the XRPD profile of 14-A1 (Experiment Reference14-Sample Reference A1) (wet sample, disordered Pattern #23).

FIG. 256 depicts the XRPD profile of 14-A2 (Experiment Reference14-Sample Reference A2) (oven dried sample, Pattern #23).

FIG. 257 depicts the XRPD profile of 14-B1 (Experiment Reference14-Sample Reference B1) (wet sample, disordered Pattern #23).

FIG. 258 depicts the XRPD profile of 14-B2 (Experiment Reference14-Sample Reference B2) (oven dried sample, Pattern #23).

FIG. 259 depicts the XRPD profile of 14-C1 (Experiment Reference14-Sample Reference C1) (wet sample, high background Pattern #6a).

FIG. 260 depicts the XRPD profile of 14-C2 (Experiment Reference14-Sample Reference C2) (oven dried sample, Pattern #6a).

FIG. 261 depicts the 14-A (Experiment Reference 14-Sample Reference A)showed a solid in the bottom of the vial after 6 days.

FIG. 262 depicts the 14-B (Experiment Reference 14-Sample Reference B)showed lots of small solid pellets in the bottom of the vial after 6days.

FIG. 263 depicts the 14-C(Experiment Reference 14-Sample Reference C)showed a wet powder in the bottom of the vial after 6 days.

FIG. 264 depicts the XRPD diffractogram overlay of 14-A1 (ExperimentReference 14-Sample Reference A1) (disordered Pattern #23) and 14-A2(Experiment Reference 14-Sample Reference A2) (Pattern #23).

FIG. 265 depicts the XRPD diffractogram overlay of 14-B1 (ExperimentReference 14-Sample Reference B1) (disordered Pattern #23) and 14-B2(Experiment Reference 14-Sample Reference B2) (Pattern #23).

FIG. 266 depicts the XRPD diffractogram overlay of 14-C1 (ExperimentReference 14-Sample Reference C1) (high background Pattern #6a) and14-C2 (Experiment Reference 14-Sample Reference C2) (Pattern #6a).

FIG. 267 depicts the XRPD profile of 15-T0 (Experiment Reference15-Sample Reference T0) (Pattern #1, Sample Reference 1).

FIG. 268 depicts the XRPD profile of 15-T9 (Experiment Reference15-Sample Reference T9) (amorphousised Pattern #1).

FIG. 269 depicts the XRPD profile of 15-T18 (Experiment Reference15-Sample Reference T18) (amorphousised Pattern #1).

FIG. 270 depicts the XRPD profile of 15-T27 (Experiment Reference15-Sample Reference T27) (amorphousised Pattern #1).

FIG. 271 depicts the XRPD profile of 15-T33 (Experiment Reference15-Sample Reference T33) (amophousised Pattern #1).

FIG. 272 depicts the XRPD diffractogram overlay of the various timepoints of, from bottom to top, Experiment Reference 15 (T=0 (SampleReference 1), T=9 min, T=18 min, T=27 min, T=33 h), wherein 15-T0(Experiment Reference 15-Sample Reference T0); 15-T9 (ExperimentReference 15-Sample Reference T9); 15-T18 (Experiment Reference15-Sample Reference T18); 15-T27 (Experiment Reference 15-SampleReference T27) and 15-T33 (Experiment Reference 15-Sample ReferenceT33).

FIG. 273 depicts the XRPD profile of 16-A1 (wet sample, t=24 h)(Experiment Reference 16-Sample Reference A1).

FIG. 274 depicts the XRPD profile of 16-A2 (wet sample, t=48 h)(Experiment Reference 16-Sample Reference A2).

FIG. 275 depicts the XRPD profile of 16-A3 (wet sample, t=108 h)(Experiment Reference 16-Sample Reference A3).

FIG. 276 depicts the XRPD profile of 16-A4 (wet sample, t=192 h)(Experiment Reference 16-Sample Reference A4).

FIG. 277 depicts the XRPD profile of 16-A8 (wet sample, t=4 weeks)(Experiment Reference 16-Sample Reference A8).

FIG. 278 depicts the XRPD profile of 16-B1 (wet sample, t=24 h)(Experiment Reference 16-Sample Reference B1).

FIG. 279 depicts the XRPD profile of 16-B2 (wet sample, t=48 h)(Experiment Reference 16-Sample Reference B2).

FIG. 280 depicts the XRPD profile of 16-B3 (wet sample, t=108 h)(Experiment Reference 16-Sample Reference B3).

FIG. 281 depicts the XRPD profile of 16-B4 (wet sample, t=192 h).(Experiment Reference 16-Sample Reference B4).

FIG. 282 depicts the XRPD profile of 16-B8 (wet sample, t=4 weeks)(Experiment Reference 16-Sample Reference B8).

FIG. 283 depicts the timepoints of the suspension equilibration in tBMEat 20° C. XRPD diffractogram overlay of, from top to bottom, Sample B-A2(Form B, Pattern #2a), 8-A4 (Form A, Pattern #6a), 16-A1 (t=24 h, 16-A2(t=48 h), 16-A3 (t=108 h), 16-A4 (t=192 h) 16-A8 (t=4 weeks).

FIG. 284 depicts the timepoints of the suspension equilibration in tBMEat 40° C. XRPD diffractogram overlay of, from top to bottom, Sample B-A2(Form B, Pattern #2a), 8-A4 (Form A, Pattern #6a), 16-B1 (t=24 h, 16-B2(t=48 h), 16-B3 (t=108 h), 16-B4 (t=192 h) 16-B8 (t=4 weeks).

FIG. 285 depicts the crystal data for 11-M2 (Experiment Reference11-Sample Reference M2).

FIG. 286 depicts the crystal data for 11-Q2 (Experiment Reference11-Sample Reference Q2).

FIG. 287 depicts the crystal structure of the tabernanthalogmonofumarate salt (Pattern #6a, Form A).

FIG. 288 depicts the hydrogen bonding network of the tabernanthalogmonofumarate salt (Pattern #6a, Form A).

FIG. 289 depicts the comparison of simulated powder pattern 11-M2(Experiment Reference 11-Sample Reference M2, top) and experimentallyobtained powder diffraction pattern for 6-S2 (Experiment Reference6-Sample Reference S2) (Form A, Pattern #6a, reference, bottom).

FIG. 289A depicts the XRPD diffractogram overlay of simulated powderdiffraction pattern (bottom, 11-M2 (Experiment Reference 11-SampleReference M2), Form A) and 6-S2 ((Experiment Reference 6-SampleReference S2), top, Form A reference).

FIG. 290 depicts the SCXRD (11-M2 (Experiment Reference 11-SampleReference M2)), structural void analyses.

FIG. 291 depicts the crystal structure of tabernanthalog hemifumarate(Pattern #14, Form I).

FIG. 292 depicts the hydrogen bonding network of tabernanthaloghemifumarate (Pattern #14, Form I).

FIG. 293 depicts the comparison of simulated powder pattern 11-Q2(Experiment Reference 11-Sample Reference Q2) and experimentallyobtained powder diffraction pattern for 5-B3 (Experiment Reference5-Sample Reference B3).

FIG. 293A depicts the XRPD diffractogram overlay of simulated powderdiffraction pattern 11-Q2 (Experiment Reference 11-Sample Reference Q2),bottom, Form I) and 5-B3 ((Experiment Reference 5-Sample Reference B3),top, Form I reference).

FIG. 294 depicts the SCXRD (11-Q2 (Experiment Reference 11-SampleReference Q2)), structural void analyses.

FIG. 295 depicts the Q NMR assay (vs TCNB) of the tabernanthalogmonofumarate salt (Sample Reference 1, Pattern #1, 93.13% w/w), spectrumwas acquired in DMSO-d₆ and calibrated to the non-deuterated solventresidual at 2.50 ppm. API to Fumaric acid, 1.0 to 1.0.

FIG. 296 depicts the ¹H NMR of the tabernanthalog monofumarate salt(Sample Reference 1, Pattern #1), spectrum was acquired in DMSO-d₆ andcalibrated to the non-deuterated solvent residual at 2.50 ppm.Acetonitrile content calculated 0.2% w/w.

FIG. 297 depicts the XRPD profile of the tabernanthalog monofumaratesalt (Sample Reference 1, Pattern #1).

FIG. 298 depicts the XRPD profile of the tabernanthalog monofumaratesalt ground (Sample Reference 1, Pattern #1).

FIG. 299 depicts the TGA profile of the tabernanthalog monofumarate salt(Sample Reference 1, Pattern #1, not ground), analysis was acquired at aramp rate of +10° C./minute. The first TG event (−2.1% w/w) wasconsistent with the release of volatiles, potentially water and solvent(water −2.6% w/w+acetonitrile −0.2% w/w). Significant weight loss wasobserved at higher temperature (>200° C.), attributed to chemicaldegradation and ablation of the sample.

FIG. 300 depicts the DSC of the tabernanthalog monofumarate salt(Pattern #1, Sample Reference 1, not ground), analysis was acquired at aramp rate of +10° C./minute.

FIG. 301 depicts the DVS profiles of the tabernanthalog monofumaratesalt (Pattern #1, Sample Reference 1, not ground).

FIG. 302 : depicts the PLM of the tabernanthalog monofumarate salt(Pattern #1, Sample Reference 1, not ground), normal polarized(magnification×2).

FIG. 303 depicts the PLM of the tabernanthalog monofumarate salt(Pattern #1, Sample Reference 1, not ground), cross polarized(magnification×5).

FIG. 304 depicts the SEM surface topography of the tabernanthalogmonofumarate salt (Pattern #1, Sample Reference 1, not ground),resolution at 150×.

FIG. 305 depicts the SEM surface topography of the tabernanthalogmonofumarate salt (Pattern #1, Sample Reference 1, not ground),resolution at 500×.

FIG. 306 depicts the SEM surface topography of the tabernanthalogmonofumarate salt (Pattern #1, Sample Reference 1, not ground),resolution at 1000×.

FIG. 307 depicts the SEM surface topography of the tabernanthalogmonofumarate salt (Pattern #1, Sample Reference 1, not ground),resolution at 2500×.

FIG. 308 depicts the HPLC profile of the tabernanthalog monofumaratesalt (Pattern #1, Sample Reference 1, not ground).

FIG. 309 depicts the ¹H NMR spectrum of 7-N2 (Experiment Reference7-Sample Reference N2) (suspended in 2-MeTHF), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm API to Fumaric acid, 1.0 to 1.0. 2-MeTHF n.d.

FIG. 311 depicts the TGA profile of 7-N2 (Experiment Reference 7-SampleReference N2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 312 depicts the DSC profile of 7-N2 (Experiment Reference 7-SampleReference N2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 313 depicts the ¹H NMR spectrum of 7-B2 (Experiment Reference7-Sample Reference B2) (suspended in MeCN), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. API to Fumaric acid, 1.0 to 1.0, 0.03% w/w MeCN content.

FIG. 315 depicts the TGA profile of 7-B2 (Experiment Reference 7-SampleReference B2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 316 depicts the DSC profile of 7-B2 (Experiment Reference 7-SampleReference B2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 317 depicts the ¹H NMR spectrum of 6-G2 (Experiment Reference6-Sample Reference G2) (suspended in ethyl acetate), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 1.0. Residual ethylacetate (3.2% w/w).

FIG. 319 depicts the TGA profile of 6-G2 (Experiment Reference 6-SampleReference G2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 320 depicts the DSC profile of 6-G2 (Experiment Reference 6-SampleReference G2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 321 depicts the ¹H NMR spectrum of 1-P2 (Experiment Reference1-Sample Reference P2) (crystallized from water, oven dried), analysiswas acquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 1.0. Residualacetonitrile (0.2% w/w).

FIG. 322 depicts the XRPD profile of 1-P2 (Experiment Reference 1-SampleReference P2).

FIG. 323 depicts the XRPD overlay of, from bottom to top, thetabernanthalog fumarate salt (Sample Reference 1), 1-P1 (ExperimentReference 1-Sample Reference P1) (wet pellet) and 1-P2 (ExperimentReference 1-Sample Reference P2) (oven dried) [Key differences: 16.7°,19.3°2θ; approx. isostructural].

FIG. 324 depicts the TGA profile of 1-P2 (Experiment Reference 1-SampleReference P2), analysis was acquired at a ramp rate of +10° C./minute(Approximately flat baseline, preceding melt, likely to be anhydrousform).

FIG. 325 depicts the DSC profile of 1-P2 (Experiment Reference 1-SampleReference P2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 326 depicts the XRPD profile of 7-H1 (Experiment Reference 7-SampleReference H1).

FIG. 327 depicts the ¹H NMR spectrum of 6-R2 (Experiment Reference6-Sample Reference R2) (suspended in toluene), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm API to Fumaric acid, 1.0 to 1.0. Residual toluene (4.6% w/w).

FIG. 329 depicts the TGA profile of 6-R2 (Experiment Reference 6-SampleReference R2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 330 depicts the DSC profile of 6-R2 (Experiment Reference 6-SampleReference R2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 331 depicts the ¹H NMR spectrum of 6-K2 (Experiment Reference6-Sample Reference K2) (suspended in methanol), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm API to Fumaric acid, 1.0 to 1.0. Residual methanol (0.2% w/w).

FIG. 333 depicts the TGA profiles of 6-K2 (Experiment Reference 6-SampleReference K2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 334 depicts the DSC profile of 6-K2 (Experiment Reference 6-SampleReference K2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 335 depicts the ¹H NMR spectrum of 6-O2 (Experiment Reference6-Sample Reference O2) (suspended in nitromethane), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. API to Fumaric acid, 1.0 to 1.0. Residualnitromethane (0.2% w/w).

FIG. 337 depicts the TGA profile of 6-02 (Experiment Reference 6-SampleReference O2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 338 depicts the DSC profile of 6-02 (Experiment Reference 6-SampleReference O2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 344 depicts the ¹H NMR spectrum of 6-S2 (Experiment Reference6-Sample Reference S2) (suspended in water), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm API to Fumaric acid, 1.0 to 1.0. and was anhydrous and solvent free.Small decrease in the impurity burden was observed in aryl and aliphaticregions, post crystallization.

FIG. 345 depicts the ¹H NMR spectra overlay of 6-S2 (ExperimentReference 6-Sample Reference S2) (suspended in water, top) and suppliedtabernanthalog monofumarate salt (Sample Reference 1, bottom), analysiswas acquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm.

FIG. 346(A) depicts the overlay of XRPD profiles of a calculated powderpattern for tabernanthalog monofumarate, Pattern #6a, Form A (top) and6-S2 (bottom).

FIG. 346(B) depicts the overlay of experimental and simulated patternsof tabernanthalog monofumarate (Pattern #6a, Form A).

FIG. 347 depicts the TGA profile of 6-S2 (Experiment Reference 6-SampleReference S2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 348 depicts the DSC profile of 6-S2 (Experiment Reference 6-SampleReference S2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 349 depicts the ¹H NMR spectrum of 1-K2 (Experiment Reference1-Sample Reference K2) (crystallized from methanol), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 1.0. Specimen contained0.7% w/w methanol, (th. solvate calc., 8.5% w/w). Residual acetonitrile(0.3% w/w).

FIG. 350 depicts the XRPD profile of 1-K2 (Experiment Reference 1-SampleReference K2) (oven dried) [Form A (Isostructural+reflections 8.2°,11.4°2θ].

FIG. 351 depicts the XRPD overlay of, from bottom to top, thetabernanthalog monofumarate salt (Sample Reference 1), 1-K1 (ExperimentReference 1-Sample Reference K1) (wet pellet) and 1-K2 (ExperimentReference 1-Sample Reference K2) (oven dried). Key differences: 8.2°,13.0°, 16.6°, 19.5°, 20.7°, 25.3°, 26.0°2θ.

FIG. 352 depicts the TGA profile of 1-K2 (Experiment Reference 1-SampleReference K2), analysis was acquired at a ramp rate of +10° C./minute(Flat baseline (anhydrous)).

FIG. 353 depicts the DSC profile of 1-K2 (Experiment Reference 1-SampleReference K2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 354 depicts the XRPD profile of 6-N1 (Experiment Reference 6-SampleReference N1) (wet pellet). 6-N1 converted to Pattern #1 uponoven-drying (6-N2) (Experiment Reference 6-Sample Reference N2).

FIG. 355 depicts the ¹H NMR spectrum of (6-J2) (Experiment Reference6-Sample Reference J2) (suspended in isopropyl acetate), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 1.0. Residual isopropylacetate 10.0% w/w. (th. solvate calc., 22.8% w/w).

FIG. 357 depicts the TGA profiles of 6-J2 (Experiment Reference 6-SampleReference J2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 358 depicts the DSC profile of 6-J2 (Experiment Reference 6-SampleReference J2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 359 depicts the XRPD profile of 6-G1 (Experiment Reference 6-SampleReference G1) (oven dried). 6-G1 converted to Pattern #2b uponoven-drying (7-G2) (Experiment Reference 7-Sample Reference G2).

FIG. 360 depicts the XRPD profile of 6-P1 (Experiment Reference 6-SampleReference P1).

FIG. 361 depicts the XRPD profile of 6-Q1 (Experiment Reference 6-SampleReference Q1).

FIG. 362 depicts the XRPD profile of (6-A1) (Experiment Reference6-Sample Reference A1). 6-A1 converted to Pattern #2b upon oven-drying(6-A2) (Experiment Reference 6-Sample Reference A2).

FIG. 363 depicts the XRPD profile of 7-L1 (Experiment Reference 7-SampleReference L1).

FIG. 368 depicts the ¹HNMR spectrum of (1-C2) (Experiment Reference1-Sample Reference C2) (crystallised from butanol), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 1.0. Specimen contained6.3% w/w butanol, (th. solvate calc., 13.7% w/w). Acetonitrile could notbe quantified due to co-resonant signal.

FIG. 370 depicts the XRPD overlay of, form bottom to top, thetabernanthalog monofumarate salt (Pattern #1, Sample Reference 1), 1-C1(Experiment Reference 1-Sample Reference C1) (wet pellet) and (1-C2)(Experiment Reference 1-Sample Reference C2) (oven dried). Keydifferences: 8.4°, 9.4°, 10.7°, 11.1°, 16.9°, 23.4°, 24.5°2θ.

FIG. 371 depicts the TGA profiles of 1-C2 (Experiment Reference 1-SampleReference C2), analysis was acquired at a ramp rate of +10° C./minute.Weight loss transition (−8.6% w/w) attributed in part to butanolrelease. Probable butanol, hemi-solvate.

FIG. 372 depicts the DSC of 1-C2 (Experiment Reference 1-SampleReference C2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 373 depicts the XRPD profile of 1-F1 (Experiment Reference 1-SampleReference F1).

FIG. 374 depicts the XRPD profile of 7-01 (Experiment Reference 7-SampleReference 01).

FIG. 375 depicts the XRPD profile of tabernanthalog DSC XRPD 150C(Sample Reference 1), cold cryst., 150° C.

FIG. 376 depicts the XRPD profile of 7-A1 (Experiment Reference 7-SampleReference A1); High disorder. 7-A1 remained as Pattern #19 uponoven-drying (7-A2) (Experiment Reference 7-Sample Reference A2)

FIG. 377 depicts the XRPD profile of 1-Q1.

FIG. 377A depicts the ¹H NMR spectrum of 1-G2 (Experiment Reference1-Sample Reference G2) (crystallized from ethanol), analysis wasacquired in DMSO-d₆ and calibrated to the non-deuterated solventresidual at 2.50 ppm. API to Fumaric acid, 2.0 to 1.0. Specimencontained 4.9% w/w ethanol, (th. solvate calc., 11.7% w/w). Residualacetonitrile (0.2% w/w).

FIG. 377B depicts the XRPD overlay of, from bottom to top, thetabernanthalog monofumarate salt (Pattern #1, Sample Reference 1), 1-G1(Experiment Reference 1-Sample Reference G1) (wet pellet) and 1-G2(Experiment Reference 1-Sample Reference G2) (oven dried). Keydifferences: 8.2°, 11.1°, 15.5°, 17.0°, 21.6°2θ.

FIG. 377C depicts the TGA profile of 1-G2 (Experiment Reference 1-SampleReference G2), analysis was acquired at a ramp rate of +10° C./minute.Weight loss transition (−5.8% w/w) attributed to ethanol release.Probable ethanol, hemi-solvate.

FIG. 377D depicts the DSC profile of 1-G2 (Experiment Reference 1-SampleReference G2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 377E depicts the ¹H NMR spectrum of (5-B3) (Experiment Reference5-Sample Reference B3), analysis was acquired in DMSO-d₆ and calibratedto the non-deuterated solvent residual at 2.50 ppm. API to Fumaric acid,2.0 to 1.0. 0.2% w/w acetone, 0.3% w/w acetonitrile, and 2.4% w/wmethanol content.

FIG. 377F depicts the XRPD profile of (5-B3) (Experiment Reference5-Sample Reference B3).

FIG. 377G depicts the XRPD profiles of a simulated powder pattern fortabernanthalog hemifumarate, Pattern #14, Form I (11-Q2 ((ExperimentReference 11-Sample Reference Q2), top) and 5-B3 (Experiment Reference5-Sample Reference B3) (bottom).

FIG. 377H depicts the overlay of experimental and simulated patterns oftabernanthalog hemifumarate (Pattern #14, Form I).

FIG. 377I depicts the TGA profile of (5-B3) (Experiment Reference5-Sample Reference B3), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 377J depicts the DSC profile of (5-B3) (Experiment Reference5-Sample Reference B3), analysis was acquired at a ramp rate of +10°C./minute.

FIG. 378 depicts the ¹H NMR spectrum of 7-P2 (Experiment Reference7-Sample Reference P2) (suspended in isopropanol), analysis was acquiredin DMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm API to Fumaric acid, 2.0 to 1.0. Residual isopropanol 0.9% w/w.

FIG. 380 depicts the TGA profile of 7-P2 (Experiment Reference 7-SampleReference P2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 381 depicts the DSC of 7-P2 (Experiment Reference 7-SampleReference P2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 382 depicts the XRPD profile of 10-B1 (Experiment Reference10-Sample Reference B1).

FIG. 383 depicts the DSC of 10-B1 (Experiment Reference 10-SampleReference B1), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 384 depicts an XRPD diffractogram of the tabernanthalog sorbatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 216.

FIG. 385 depicts an XRPD diffractogram of the tabernanthalog tartratesalt. The XRPD signals observed in this diffractogram are characterizedin Table 217.

FIG. 386 depicts an XRPD diffractogram of the tabernanthalog malatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 219.

FIG. 387 depicts an XRPD diffractogram of the tabernanthalog tosylatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 220.

FIG. 388 depicts an XRPD diffractogram of the tabernanthalog benzoatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 218.

FIG. 389 depicts an XRPD diffractogram of the tabernanthalog adipatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 221.

FIG. 390 depicts an XRPD diffractogram of the tabernanthalog glucoronatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 222.

FIG. 391 depicts an XRPD diffractogram of the tabernanthalog phosphatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 223.

FIG. 392 depicts an XRPD diffractogram of the tabernanthalog edisylatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 224.

FIG. 393 depicts an XRPD diffractogram of tabernanthalog. The XRPDsignals observed in this diffractogram are characterized in Table 215.

FIG. 394 depicts an XRPD diffractogram of the tabernanthalog maleatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 225.

FIG. 395 depicts an XRPD diffractogram of the tabernanthalog galactaratesalt. The XRPD signals observed in this diffractogram are characterizedin Table 226.

FIG. 396 depicts an XRPD diffractogram of the tabernanthalog citratesalt. The XRPD signals observed in this diffractogram are characterizedin Table 227.

FIG. 397 depicts an XRPD diffractogram of the tabernanthalog glycolatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 228.

FIG. 398 depicts an XRPD diffractogram of the tabernanthalog succinatesalt. The XRPD signals observed in this diffractogram are characterizedin Table 229.

FIG. 399 depicts the calculated (c) pK_(a) of tabernanthalog.

FIG. 401 depicts the XRPD powder diffraction pattern of thetabernanthalog sorbate salt compared to that of non-ionizedtabernanthalog and sorbic acid.

FIG. 401 depicts the XRPD powder diffraction pattern of thetabernanthalog tartrate salt compared to that of non-ionizedtabernanthalog and L-tartaric acid.

FIG. 402 depicts the XRPD powder diffraction pattern of thetabernanthalog malate salt compared to that of non-ionizedTabernanthalog and malic acid.

FIG. 403 depicts the XRPD powder diffraction pattern of thetabernanthalog tosylate salt compared to that of non-ionizedTabernanthalog and p-toluene sulfonic acid.

FIG. 404 depicts the XRPD powder diffraction pattern of thetabernanthalog benzoate salt (2-R2; (Experiment Reference 2-SampleReference R2)) compared to that of non-ionized tabernanthalog (native)and benzoic acid.

FIG. 405 depicts the XRPD diffractogram overlay of the tabernanthalogtartrate salt, 3-A1 (Experiment Reference 3-Sample Reference A1, top)and 2-I2 (Experiment Reference 2-Sample Reference 12, bottom).

FIG. 406 depicts the XRPD diffractogram overlay of the tabernanthalogbenzoate salt, 3-B1 (Experiment Reference 3-Sample Reference B1, top)and 2-R2 (Experiment Reference 2-Sample Reference R2, bottom).

FIG. 407 depicts the XRPD diffractogram overlay of the tabernanthalogsorbate salt, 3-C1 (Experiment Reference 3-Sample Reference C1, top) and2-V2 (Experiment Reference 2-Sample Reference V2, bottom).

FIG. 408 depicts the DSC thermogram of 3-B1 (Experiment Reference3-Sample Reference B1).

FIG. 409 depicts the 1H NMR spectrum overlay of the tabernanthalogsorbate salt (4-A2; Experiment Reference 4-Sample Reference A2) (top;concordant with reference) and 3-C1 (Experiment Reference 3-SampleReference C1) (bottom)

FIG. 410 depicts the DSC thermogram overlay of the tabernanthalogsorbate salt (4-A2; Experiment Reference 4-Sample Reference A2) and 3-C1(Experiment Reference 3-Sample Reference C1).

FIG. 411 depicts the TGA thermogram overlay of the tabernanthalogsorbate salt (4-A2; Experiment Reference 4-Sample Reference A2) and 3-C1(Experiment Reference 3-Sample Reference C1).

FIG. 412 depicts the XRPD diffractogram overlay of the tabernanthalogsorbate salt (4-A2; Experiment Reference 4-Sample Reference A2;congruent with the reference pattern) with 3-C1 (Experiment Reference3-Sample Reference C1).

FIG. 413 depicts the photographs of the SIF buffer solubility panel,recorded at timepoints t=0, 1 h, 3 h, 6 h and 24 h; all dissolved exceptthe tabernanthalog benzoate salt (5-C(Experiment Reference 5-SampleReference C), 5-G (Experiment Reference 5-Sample Reference G), and 5-K(Experiment Reference 5-Sample Reference K)) in all SIF buffers. Thetabernanthalog sorbate salt (5-L; Experiment Reference 5-SampleReference L) remained suspended only in FaSSGF.

FIG. 414 depicts the XRPD diffractogram overlay of the tabernanthalogbenzoate salt (input batch 3-B1 (Experiment Reference 3-Sample ReferenceB1)) and the various time point analyses from FaSSIF (5-C(ExperimentReference 5-Sample Reference C), wet and dry pellets).

FIG. 415 depicts the XRPD diffractogram overlay of the tabernanthalogbenzoate salt (input batch 3-B1; Experiment Reference 3-Sample ReferenceB1) and the various time point analyses from FeSSIF (5-G (ExperimentReference 5-Sample Reference G), wet and dry pellets).

FIG. 416 depicts the XRPD diffractogram overlay of the tabernanthalogbenzoate salt (input batch 3-B1; Experiment Reference 3-Sample ReferenceB1) and the various time point analyses from FaSSGF (wet and drypellets). For 5-K11 (Experiment Reference 5-Sample Reference K11) (wetpellet, t=24 h), there was insufficient material for analysis.

FIG. 417 depicts the XRPD diffractogram overlay of 5-K12 (ExperimentReference 5-Sample Reference K12) (dry pellet, t=24 h, middle) withtabernanthalog (native) (top) and benzoic acid (bottom).

FIG. 418 depicts the ¹H NMR overlay of 5-K12 (Experiment Reference5-Sample Reference K12) (dry pellet, t=24 h, top) and 3-B1 (ExperimentReference 3-Sample Reference B1) (Tabernanthalog (native), input,bottom). In the ¹H NMR analysis, API peaks are absent from 5-K12.

FIG. 419 depicts the XRPD diffractogram overlay of, from bottom to top,the tabernanthalog sorbate salt (input batch 3-C1; Experiment Reference3-Sample Reference C1) and the various time point analyses from FaSSGF5-L2 (wet pellet, t=1 h), 5-L3 (dry pellet, t=1 h) 5-L5 (wet pellet, t=3h), 5-L6 (dry pellet, t=3 h), 5-L8 (wet pellet, t=6 h), 5-L9 (drypellet, t=6 h), 5-L11 (wet pellet, t=24 h), 5-L12 (dry pellet, t=24 h),wherein 5-L2 is (Experiment Reference 5-Sample Reference L2); 5-L3 is(Experiment Reference 5-Sample Reference L3); 5-L5 is (ExperimentReference 5-Sample Reference L5); 5-L6 is (Experiment Reference 5-SampleReference L6); 5-L8 is (Experiment Reference 5-Sample Reference L8);5-L9 is (Experiment Reference 5-Sample Reference L9); 5-L11 is(Experiment Reference 5-Sample Reference L11); and 5-L12 is (ExperimentReference 5-Sample Reference L12).

FIG. 420 depicts the XRPD diffractogram overlay of 5-L12 (ExperimentReference 5-Sample Reference L12) (dry pellet, t=24 h, middle) withtabernanthalog (native) (top) and sorbic acid (bottom).

FIG. 421 depicts the ¹H NMR overlay of 5-L12 (Experiment Reference5-Sample Reference L12) (dry pellet, t=24 h, top) and 3-C1 (ExperimentReference 3-Sample Reference C1, tabernanthalog sorbate salt, input,bottom). The API peaks are absent from 5-L12.

FIG. 422 depicts the XRPD diffractogram overlay of, from bottom to top,8-A4 of Example 5 (Experiment Reference 8-Sample Reference A4) ofExample 5) (input, bottom), 6-A1 (Experiment Reference 6-SampleReference A1) (t=5 d, middle) and 6-A2 (Experiment Reference 6-SampleReference A2) (t=10 d, top).

FIG. 423 depicts the XRPD diffractogram overlay of 3-A1 (ExperimentReference 3-Sample Reference A1) (input, top), 6-B1 (ExperimentReference 6-Sample Reference B1) (t=5 d, bottom) and 6-B2 (ExperimentReference 6-Sample Reference B2) (t=10 d, middle).

FIG. 424 depicts the XRPD diffractogram overlay of 3-B1 (ExperimentReference 3-Sample Reference B1) (input, top), 6-C1 (ExperimentReference 6-Sample Reference C1) (t=5 d, bottom) and 6-C2 (ExperimentReference 6-Sample Reference C2) (t=10 d, middle).

FIG. 425 depicts the XRPD diffractogram overlay of 3-C1 (ExperimentReference 3-Sample Reference C1) (input, top), 6-D1 (ExperimentReference 6-Sample Reference D1) (t=5 d, bottom) and 6-D2 (ExperimentReference 6-Sample Reference D2) (t=10 d, middle).

FIG. 426 depicts the ¹H NMR spectrum overlay of [8-A4 (ExperimentReference 8-Sample Reference A4) of Example 5)] (input, bottom), 6-A1(Experiment Reference 6-Sample Reference A1) (t=5 d, middle) and 6-A2(Experiment Reference 6-Sample Reference A2) (t=10 d, top).

FIG. 427 depicts the ¹H NMR spectrum overlay of 3-A1 (ExperimentReference 3-Sample Reference A1) (input, bottom), 6-B1 (ExperimentReference 6-Sample Reference B1) (t=5 d, middle) and 6-B2 (ExperimentReference 6-Sample Reference B2) (t=10 d, top).

FIG. 428 depicts the ¹H NMR spectrum overlay of 3-B1 (ExperimentReference 3-Sample Reference B1) (input, bottom), 6-C1 (ExperimentReference 6-Sample Reference C1) (t=5 d, middle) and 6-C2 (ExperimentReference 6-Sample Reference C2) (t=10 d, top).

FIG. 429 depicts the ¹H NMR spectrum overlay of 3-C1 (ExperimentReference 3-Sample Reference C1) (input, bottom), 6-D1 (ExperimentReference 6-Sample Reference D1) (t=5 d, middle) and 6-D2 (ExperimentReference 6-Sample Reference D2) (t=10 d, top).

FIG. 430 depicts the photograph of 6-A (Experiment Reference 6-SampleReference A, fumarate), 6-B (Experiment Reference 6-Sample Reference B,tartrate), 6-C(Experiment Reference 6-Sample Reference C, benzoate), and6-D (Experiment Reference 6-Sample Reference D, sorbate) at t=0. [Notepictured loosely capped; stability panel commenced open capped.] Saltidentities: A=Fumarate, B=Tartrate, C=Benzoate, D=Sorbate.

FIG. 431 depicts the photograph of 6-A (Experiment Reference 6-SampleReference A, fumarate), 6-B (Experiment Reference 6-Sample Reference B,tartrate), 6-C(Experiment Reference 6-Sample Reference C, benzoate), and6-D (Experiment Reference 6-Sample Reference D, sorbate) at t=5 d. Saltidentities: A=Fumarate, B=Tartrate, C=Benzoate, D=Sorbate.

FIG. 432 depicts the photographs of 6-A (Experiment Reference 6-SampleReference A, fumarate), 6-B (Experiment Reference 6-Sample Reference B,tartrate), 6-C(Experiment Reference 6-Sample Reference C, benzoate), and6-D (Experiment Reference 6-Sample Reference D, sorbate) at t=10 d. Saltidentities: A=Fumarate, B=Tartrate, C=Benzoate, D=Sorbate.

FIG. 433 depicts the DVS Sorption isotherms of the tabernanthalogmonofumarate salt [Pattern #6a, Form A, 8-A4 (Experiment Reference8-Sample Reference A4) of Example 5)].

FIG. 434 depicts the DVS Desorption isotherms of the tabernanthalogtartrate salt (3-A1 (Experiment Reference 3-Sample Reference A1)).

FIG. 435 depicts the DVS Sorption isotherms of the tabernanthalogbenzoate salt (3-B1 (Experiment Reference 3-Sample Reference B1)).

FIG. 436 depicts the DVS Desorption isotherms of the tabernanthalogsorbate salt (4-A2 (Experiment Reference 4-Sample Reference A2)).

FIG. 437 depicts the calibration curve of tabernanthalog.

FIG. 438 depicts the Q ¹H NMR of tabernanthalog (native), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. Q ¹H NMR assay (vs TCNB) showed 99.0% w/w. DCMcontent 0.2% w/w. KF titre determined water content 0.2% w/w (ca. 25 mgsample analyzed).

FIG. 439 depicts the DSC profile of tabernanthalog (native), analysiswas acquired at a ramp rate of +10° C./minute. Consistent with singlesharp melt event 149° C. (−60.6 Jg⁻¹); non-ablative, cf. Thetabernanthalog fumarate salt. The change in c_(p) at the beginning ofeach thermal segment was attributed to the weight differential betweenthe reference and sample pans.

FIG. 440 depicts the TGA profile of tabernanthalog (native), analysiswas acquired at a ramp rate of +10° C./minute. Flat baseline wasobserved<200° C. Significant weight loss was observed at highertemperature (>200° C.), attributed to chemical degradation and ablationof the sample.

FIG. 442 depicts the HPLC of tabernanthalog (native).

FIG. 443 depicts the PLM of tabernanthalog (native)×2 mag, NP.

FIG. 444 depicts the PLM of tabernanthalog (native)×20 mag, NP(Non-homogeneous optically crystalline specimen).

FIG. 445 depicts the SEM of tabernanthalog (native), resolution at 150×(wide field).

FIG. 446 depicts the SEM of tabernanthalog (native), resolution at 250×(wide field).

FIG. 447 depicts the SEM of tabernanthalog (native), resolution at 500×(wide field).

FIG. 448 depicts the SEM of tabernanthalog (native), resolution at 1000×(wide field).

FIG. 449 depicts the SEM of tabernanthalog (native), resolution at 2500×(wide field).

FIG. 450 depicts the SEM of tabernanthalog (native), resolution at 2500×(different aspect).

FIG. 451 depicts the ¹H NMR of 2-V2 (Experiment Reference 2-SampleReference V2), acquired in DMSO-d6 and calibrated to the non-deuteratedsolvent residual at 2.50 ppm. 1.0 mol of API to 1.0 mol sorbic acid.Ethanol content 0.1% w/w.

FIG. 452 depicts the ¹H NMR of tabernanthalog sorbate salt 2-V2(Experiment Reference 2-Sample Reference V2) (top spectrum), overlaidwith Tabernanthalog (native) (bottom spectrum).

FIG. 453 depicts the DSC profile of tabernanthalog sorbate salt; 2-V2(Experiment Reference 2-Sample Reference V2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 454 depicts the TGA of tabernanthalog sorbate salt, 2-V2(Experiment Reference 2-Sample Reference V2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 455 depicts the DVS of tabernanthalog sorbate salt, 4-A2(Experiment Reference 4-Sample Reference A2), kinetic plot and isothermanalysis report.

FIG. 456 depicts the DVS of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2), isothermal plot.

FIG. 458 depicts the XRPD of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2) post DVS.

FIG. 459 depicts the XRPD of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2) (post DVS 0 to 90% RH,bottom diffractogram), compared with the input sample tabernanthalogsorbate salt; 4-A2 (top diffractogram).

FIG. 460 depicts the HPLC of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1).

FIG. 461 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1)×2 mag, NP.

FIG. 462 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1)×2 mag, CP.

FIG. 463 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1)×5 mag, NP.

FIG. 464 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1)×5 mag, CP.

FIG. 465 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1)×20 mag, NP.

FIG. 466 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1)×20 mag, CP.

FIG. 467 depicts the ¹H NMR of tabernanthalog tartrate salt; 2-I2(Experiment Reference 2-Sample Reference I2), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol L-tartaric acid. Ethanol content 0.1%w/w.

FIG. 468 depicts the ¹H NMR of tabernanthalog tartrate salt; 2-I2(Experiment Reference 2-Sample Reference 12) (top spectrum), overlaidwith Tabernanthalog (native) (bottom spectrum).

FIG. 469 depicts the DSC profile of tabernanthalog tartrate salt; 2-I2(Experiment Reference 2-Sample Reference I2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 470 depicts the TGA of tabernanthalog tartrate salt; 2-I2(Experiment Reference 2-Sample Reference I2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 471 depicts the DVS of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1), kinetic plot and isothermanalysis report.

FIG. 472 depicts the DVS of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1), isothermal plot FIG. 474depicts the XRPD of tabernanthalog tartrate salt; 3-A1 (ExperimentReference 3-Sample Reference A1) post DVS.

FIG. 475 depicts the XRPD of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1) post DVS 0 to 90% RH, topdiffractogram), compared with the input sample of tabernanthalogtartrate salt; 3-A1 (bottom diffractogram).

FIG. 476 depicts the HPLC of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1).

FIG. 477 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1)×2 mag, NP.

FIG. 478 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1)×2 mag, CP.

FIG. 479 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1)×5 mag, NP.

FIG. 480 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1)×5 mag, CP.

FIG. 481 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1)×5 mag, NP.

FIG. 482 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1)×5 mag, CP.

FIG. 483 depicts the ¹H NMR of tabernanthalog benzoate salt; 2-R2(Experiment Reference 2-Sample Reference R2), acquired in DMSO-d6 andcalibrated to the non-deuterated solvent residual at 2.50 ppm. 1.0 molof API to 1.0 mol of benzoic acid. Ethanol content 0.1% w/w.

FIG. 484 depicts the ¹H NMR of tabernanthalog benzoate salt; 2-R2(Experiment Reference 2-Sample Reference R2) (top spectrum), overlaidwith Tabernanthalog (native) (bottom spectrum). Depreciation in impurityburden is observed.

FIG. 485 depicts the DSC profile of tabernanthalog benzoate salt; 2-R2(Experiment Reference 2-Sample Reference R2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 486 depicts the TGA of tabernanthalog benzoate salt; 2-R2(Experiment Reference 2-Sample Reference R2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 486(A) depicts the DVS of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1), kinetic plot and isothermanalysis report.

FIG. 486B) depicts the DVS of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1), isothermal plot.

FIG. 486(C) depicts the XRPD of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1) post DVS.

FIG. 486(D) depicts the XRPD of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1) (post DVS 0 to 90% RH,bottom diffractogram), compared with the input sample of tabernanthalogbenzoate salt; 3-B1 (top diffractogram).

FIG. 486(E) depicts the HPLC of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1).

FIG. 486(F) depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1)×2 mag, NP.

FIG. 486(G) depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1)×2 mag, CP.

FIG. 486(H) depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1)×5 mag, NP.

FIG. 486(I) depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1)×5 mag, CP.

FIG. 486(J) depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1)×5 mag, NP.

FIG. 486(K) depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1)×5 mag, CP. FIG. 488 depictsthe ¹H NMR of tabernanthalog malate salt; 2-O2 (Experiment Reference2-Sample Reference O2), acquired in DMSO-d6 and calibrated to thenon-deuterated solvent residual at 2.50 ppm. 1.0 mol of API to 1.0 molL-malic acid. Ethanol content 0.2% w/w.

FIG. 488 depicts the ═H NMR of tabernanthalog malate salt; 2-O2(Experiment Reference 2-Sample Reference O2), acquired in DMSO-d6 andcalibrated to the non-deuterated solvent residual at 2.50 ppm. 1.0 molof API to 1.0 mol L-malic acid. Ethanol content 0.2% w/w.

FIG. 489 depicts the ¹H NMR of tabernanthalog malate salt; 2-O2(Experiment Reference 2-Sample Reference O2) (top spectrum), overlaidwith Tabernanthalog (native) (bottom spectrum). The comparison shows aslight appreciation in impurity burden compared to the free base.

FIG. 490 depicts the DSC profile of tabernanthalog malate salt; 2-O2(Experiment Reference 2-Sample Reference O2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 491 depicts the TGA of tabernanthalog malate salt; 2-O2 (ExperimentReference 2-Sample Reference O2), analysis was acquired at a ramp rateof +10° C./minute.

FIG. 492 depicts the XRPD of tabernanthalog malate salt; 2-O2(Experiment Reference 2-Sample Reference O2).

FIG. 493 depicts the ¹H NMR of tabernanthalog tosylate salt; 2-E2(Experiment Reference 2-Sample Reference E2), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of p-toluenesulfonic acid. Ethanolcontent 0.1% w/w.

FIG. 494 depicts the ¹H NMR of tabernanthalog tosylate salt; 2-E2(Experiment Reference 2-Sample Reference E2) (top spectrum), overlaidwith Tabernanthalog (native) (bottom spectrum).

Slight appreciation in impurity burden compared to the free base isshown.

FIG. 495 depicts the DSC profile of tabernanthalog tosylate salt; 2-E2(Experiment Reference 2-Sample Reference E2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 496 depicts the TGA of tabernanthalog tosylate salt; 2-E2(Experiment Reference 2-Sample Reference E2), analysis was acquired at aramp rate of +10° C./minute. Small −Δ wt., not solvent, attributed towater from hydrated p-toluenesulfonic acid.

FIG. 496A depicts the XRPD of tabernanthalog tosylate salt (2-E2;Experiment Reference 2-Sample Reference E2). Highly crystalline, lowangle reflection dominated, probably due to particle effects.Diffraction pattern should improve with increased powder averaging.

FIG. 509 depicts the ¹H NMR of tabernanthalog adipate salt; 2-U2(Experiment Reference 2-Sample Reference U2), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of adipic acid. Ethanol content 0.3% w/w.

FIG. 510 depicts the ¹H NMR of tabernanthalog adipate salt; 2-U2(Experiment Reference 2-Sample Reference U2) (top spectrum), overlaidwith Tabernanthalog (native) (bottom spectrum).

FIG. 511 depicts the DSC profile of tabernanthalog adipate salt; 2-U2(Experiment Reference 2-Sample Reference U2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 512 depicts the TGA of tabernanthalog adipate salt; 2-U2(Experiment Reference 2-Sample Reference U2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 514 depicts the ¹H NMR of tabernanthalog glucuronate salt; 2-M2(Experiment Reference 2-Sample Reference M2), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 0.7 mol of D-glucuronic acid (counterionstoichiometry<unity+appreciation in impurity burden). Ethanol content0.2% w/w.

FIG. 515 depicts the ¹H NMR of tabernanthalog glucuronate salt; 2-M2(Experiment Reference 2-Sample Reference M2) (top spectrum), overlaidwith tabernanthalog (native) (bottom spectrum).

FIG. 516 depicts the DSC profile of tabernanthalog glucuronate salt;2-M2 (Experiment Reference 2-Sample Reference M2), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 517 depicts the TGA of tabernanthalog glucuronate salt; 2-M2(Experiment Reference 2-Sample Reference M2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 519 depicts the ¹H NMR of tabernanthalog phosphate salt; 2-H2(Experiment Reference 2-Sample Reference H2), acquired in DMSO-d6 andcalibrated to the non-deuterated solvent residual at 2.50 ppm. 1.0 molof API to 0.7 mol of phosphoric acid. Ethanol content 0.3% w/w.Counterion stoichiometry<unity+appreciation in impurity burden.

FIG. 520 depicts the ¹H NMR of tabernanthalog phosphate salt; 2-H2(Experiment Reference 2-Sample Reference H2) (top spectrum), overlaidwith Tabernanthalog (native) (bottom spectrum).

FIG. 521 depicts the DSC profile of tabernanthalog phosphate salt; 2-H2(Experiment Reference 2-Sample Reference H2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 522 depicts the TGA of tabernanthalog phosphate salt; 2-H2(Experiment Reference 2-Sample Reference H2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 524 depicts the ¹H NMR of tabernanthalog edisylate salt; 2-J2(Experiment Reference 2-Sample Reference J2), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of ethane-1,2-disulfonic acid. Ethanolcontent 0.4% w/w.

FIG. 525 depicts the ¹H NMR of tabernanthalog edisylate salt; 2-J2(Experiment Reference 2-Sample Reference J2) (top spectrum; smalldecrease in the impurity burden was observed in aryl and aliphaticregions), overlaid with Tabernanthalog (native) (bottom spectrum).

FIG. 526 depicts the DSC profile of tabernanthalog edisylate salt; 2-J2(Experiment Reference 2-Sample Reference J2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 527 depicts the TGA of tabernanthalog edisylate salt; 2-J2(Experiment Reference 2-Sample Reference J2), analysis was acquired at aramp rate of +10° C./minute. −Δ wt., attributed to water release,originating from hydrated counter ion (EDSA·2H₂O).

FIG. 529 depicts the XRPD of the tabernanthalog sulfate salt, 2-C2(Experiment Reference 2-Sample Reference C2) (amorphous).

FIG. 535 depicts the DSC profile of 2-G2 (Experiment Reference 2-SampleReference G2; the tabernanthalog maleate salt), analysis was acquired ata ramp rate of +10° C./minute.

FIG. 536 depicts the DSC profile of 2-K2 (Experiment Reference 2-SampleReference K2; the tabernanthalog galactarate salt), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 537 depicts the DSC profile of 2-L2 (Experiment Reference 2-SampleReference L2; the tabernanthalog citrate salt), analysis was acquired ata ramp rate of +10° C./minute.

FIG. 538 depicts the DSC profile of 2-N2 (Experiment Reference 2-SampleReference N2; the tabernanthalog glycolate salt), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 539 depicts the DSC profile of 2-S2 (Experiment Reference 2-SampleReference S2; the tabernanthalog succinate salt), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 540 depicts the TGA of the tabernanthalog maleate salt (2-G2;Experiment Reference 2-Sample Reference G2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 541 depicts the TGA of the tabernanthalog galactarate salt (2-K2;Experiment Reference 2-Sample Reference K2)), analysis was acquired at aramp rate of +10° C./minute.

FIG. 542 depicts the TGA of the tabernanthalog citrate salt (2-L2;Experiment Reference 2-Sample Reference L2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 543 depicts the TGA of the tabernanthalog glycolate salt (2-N2;Experiment Reference 2-Sample Reference N2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 544 depicts the TGA of the tabernanthalog succinate salt (2-S2;Experiment Reference 2-Sample Reference S2), analysis was acquired at aramp rate of +10° C./minute.

FIG. 545 depicts the ¹H NMR of 3-A1 (Experiment Reference 3-SampleReference A1) (The tabernanthalog tartrate salt), analysis was acquiredin DMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of L-tartaric acid. Ethanol content 0.05%w/w.

FIG. 546 depicts the ¹H NMR of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1) (top spectrum), overlaidwith tabernanthalog tartrate salt; 2-I2 (Experiment Reference 2-SampleReference 12) (bottom spectrum).

FIG. 547 depicts the ¹H NMR of 3-B1 (Experiment Reference 3-SampleReference B1) (The tabernanthalog benzoate salt), analysis was acquiredin DMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of benzoic acid. Ethanol content 0.3%w/w.

FIG. 548 depicts the ¹H NMR of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1) (top spectrum), overlaidwith tabernanthalog benzoate salt; 2-R2 (Experiment Reference 2-SampleReference R2) (bottom spectrum).

FIG. 549 depicts the ¹H NMR of 3-C1 (Experiment Reference 3-SampleReference C1; the tabernanthalog sorbate salt), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of sorbic acid. Ethanol content 0.3% w/w.

FIG. 550 depicts the ¹H NMR of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1; top spectrum), overlaidwith tabernanthalog sorbate salt; 2-V2 (Experiment Reference 2-SampleReference V2; bottom spectrum).

FIG. 551 depicts the DSC profile of 3-A1 (Experiment Reference 3-SampleReference A1; the tabernanthalog tartrate salt), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 552 depicts the DSC profile of 3-B1 (Experiment Reference 3-SampleReference B1; the tabernanthalog benzoate salt), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 553 depicts the DSC profile of 3-C1 (Experiment Reference 3-SampleReference C1; the tabernanthalog benzoate salt), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 554 depicts the DSC profile of 3-B1 (Experiment Reference 3-SampleReference B1; the tabernanthalog benzoate salt), analysis was acquiredat a ramp rate of +10° C./minute from 20° C. to 220° C., 220° C. to 20°C. and 20° C. to 300° C.

FIG. 555 depicts the TGA of 3-A1 (Experiment Reference 3-SampleReference A1; the tabernanthalog tartrate salt), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 556 depicts the TGA of 3-B1 (Experiment Reference 3-SampleReference B1; the tabernanthalog benzoate salt), analysis was acquiredat a ramp rate of +10° C./minute.

FIG. 557 depicts the TGA of 3-C1 (Experiment Reference 3-SampleReference C1; the tabernanthalog sorbate salt), analysis was acquired ata ramp rate of +10° C./minute.

FIG. 558 depicts the XRPD 3-A1 (Experiment Reference 3-Sample ReferenceA1; the tabernanthalog tartrate salt).

FIG. 559 depicts the XRPD 3-B1 (Experiment Reference 3-Sample ReferenceB1; the tabernanthalog benzoate salt).

FIG. 560 depicts the XRPD 3-C1 (Experiment Reference 3-Sample ReferenceC1; the tabernanthalog sorbate salt).

FIG. 561 depicts the ¹H NMR of tabernanthalog sorbate salt; 4-A1(Experiment Reference 4-Sample Reference A1), analysis was acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of sorbic acid. Ethanol content 0.2% w/w.

FIG. 562 depicts the ¹H NMR of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2), acquired in DMSO-d6 andcalibrated to the non-deuterated solvent residual at 2.50 ppm. 1.0 molof API to 1.0 mol of sorbic acid. Ethanol content 0.1% w/w.

FIG. 563 depicts the DSC profile of 4-A2 (Experiment Reference 4-SampleReference A2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 564 depicts the TGA of 4-A2 (Experiment Reference 4-SampleReference A2), analysis was acquired at a ramp rate of +10° C./minute.

FIG. 565 depicts the XRPD 4-A2 (Experiment Reference 4-Sample ReferenceA2; the tabernanthalog sorbate salt).

FIG. 566 depicts the HPLC of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2).

FIG. 567 depicts the PLM of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2)×2 mag, NP.

FIG. 568 depicts the PLM of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2)×2 mag, CP.

FIG. 569 depicts the PLM of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2)×5 mag, NP.

FIG. 570 depicts the PLM of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2)×5 mag, CP.

FIG. 571 depicts the PLM of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2)×5 mag, NP.

FIG. 572 depicts the PLM of tabernanthalog sorbate salt; 4-A2(Experiment Reference 4-Sample Reference A2)×5 mag, CP.

FIG. 573 depicts the XRPD profile of 5-C3 (Experiment Reference 5-SampleReference C3; the tabernanthalog benzoate salt in FaSSIF, t=1 h, drypellet).

FIG. 574 depicts the XRPD profile of 5-G3 (Experiment Reference 5-SampleReference G3; the tabernanthalog benzoate salt in FeSSIF, t=1 h, drypellet).

FIG. 575 depicts the XRPD 5-K3 (Experiment Reference 5-Sample ReferenceK3; the tabernanthalog benzoate salt in FaSSGF, t=1 h, dry pellet).

FIG. 576 depicts the XRPD 5-L3 (Experiment Reference 5-Sample ReferenceL3; the tabernanthalog sorbate salt in FaSSGF, t=1 h, dry pellet).

FIG. 577 depicts the XRPD 5-C6 (Experiment Reference 5-Sample ReferenceC6; the tabernanthalog benzoate salt in FaSSIF, t=3 h, dry pellet).

FIG. 578 depicts the XRPD 5-G6 (Experiment Reference 5-Sample ReferenceG6; the tabernanthalog benzoate salt in FeSSIF, t=3 h, dry pellet).

FIG. 579 depicts the XRPD 5-K6 (Experiment Reference 5-Sample ReferenceK6; the tabernanthalog benzoate salt in FaSSGF, t=3 h, dry pellet).

FIG. 580 depicts the XRPD 5-L6 (Experiment Reference 5-Sample ReferenceL6; the tabernanthalog sorbate salt in FaSSGF, t=3 h, dry pellet).

FIG. 581 depicts the XRPD 5-C9 (Experiment Reference 5-Sample ReferenceC9; the tabernanthalog benzoate salt in FaSSIF, t=6 h, dry pellet).

FIG. 582 depicts the XRPD 5-G9 (Experiment Reference 5-Sample ReferenceG9; the tabernanthalog benzoate salt in FeSSIF, t=6 h, dry pellet).

FIG. 583 depicts the XRPD 5-K9 (Experiment Reference 5-Sample ReferenceK9; the tabernanthalog benzoate salt in FaSSGF, t=6 h, dry pellet).

FIG. 584 depicts the XRPD 5-L9 (Experiment Reference 5-Sample ReferenceL9; the tabernanthalog sorbate salt in FaSSGF, t=6 h, dry pellet).

FIG. 585 depicts the XRPD 5-C12 (Experiment Reference 5-Sample ReferenceC12; the tabernanthalog benzoate salt in FaSSIF, t=24 h, dry pellet).

FIG. 586 depicts the XRPD 5-G12 (Experiment Reference 5-Sample ReferenceG12; the tabernanthalog benzoate salt in FeSSIF, t=24 h, dry pellet).

FIG. 587 depicts the XRPD 5-K12 (Experiment Reference 5-Sample ReferenceK12; the tabernanthalog benzoate salt in FaSSGF, t=24 h, dry pellet).

FIG. 588 depicts the XRPD 5-L12 (Experiment Reference 5-Sample ReferenceL12; the tabernanthalog sorbate salt in FaSSGF, t=24 h, dry pellet).

FIG. 589 depicts the HPLC of 5-C1 (Experiment Reference 5-SampleReference C1; the tabernanthalog benzoate salt in FaSSIF, t=1 h,50×dilution).

FIG. 590 depicts the HPLC of 5-C4 (Experiment Reference 5-SampleReference C4; the tabernanthalog benzoate salt in FaSSIF, t=3 h,50×dilution).

FIG. 591 depicts the HPLC of 5-C7 (Experiment Reference 5-SampleReference C7; the tabernanthalog benzoate salt in FaSSIF, t=6 h,50×dilution).

FIG. 592 depicts the HPLC of 5-C10 (Experiment Reference 5-SampleReference C10; the tabernanthalog benzoate salt in FaSSIF, t=24 h,50×dilution).

FIG. 593 depicts the HPLC of 5-G1 (Experiment Reference 5-SampleReference G1; the tabernanthalog benzoate salt in FeSSIF, t=1 h,50×dilution).

FIG. 594 depicts the HPLC of 5-G4 (Experiment Reference 5-SampleReference G4; the tabernanthalog benzoate salt in FeSSIF, t=3 h,50×dilution).

FIG. 595 depicts the HPLC of 5-G7 (Experiment Reference 5-SampleReference G7; the tabernanthalog benzoate salt in FeSSIF, t=6 h,50×dilution).

FIG. 596 depicts the HPLC of 5-G10 (Experiment Reference 5-SampleReference G10; the tabernanthalog benzoate salt in FeSSIF, t=24 h,50×dilution).

FIG. 597 depicts the HPLC of 5-K1 (Experiment Reference 5-SampleReference K1; the tabernanthalog benzoate salt in FaSSGF, t=1 h,100×dilution).

FIG. 598 depicts the HPLC of 5-K4 (Experiment Reference 5-SampleReference K4; the tabernanthalog benzoate salt in FaSSGF, t=3 h,100×dilution).

FIG. 599 depicts the HPLC of 5-K7 (Experiment Reference 5-SampleReference K7; the tabernanthalog benzoate salt in FaSSGF, t=6 h,100×dilution).

FIG. 600 depicts the HPLC of 5-K10 (Experiment Reference 5-SampleReference K10; the tabernanthalog benzoate salt in FaSSGF, t=24 h,100×dilution).

FIG. 601 depicts the HPLC of 5-L1 (Experiment Reference 5-SampleReference L1; the tabernanthalog sorbate salt in FaSSGF, t=1 h,100×dilution).

FIG. 602 depicts the HPLC of 5-L4 (Experiment Reference 5-SampleReference L4; the tabernanthalog sorbate salt in FaSSGF, t=3 h,100×dilution).

FIG. 603 depicts the HPLC of 5-L7 (Experiment Reference 5-SampleReference L7; the tabernanthalog sorbate salt in FaSSGF, t=6 h,100×dilution).

FIG. 604 depicts the HPLC of 5-L10 (Experiment Reference 5-SampleReference L10; the tabernanthalog sorbate salt in FaSSGF, t=24 h,100×dilution).

FIG. 605 depicts the ¹H NMR of tabernanthalog monofumarate salt; 6-A1(Experiment Reference 6-Sample Reference A1) (t=5 d), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. 1.0 mol of API to 1.0 mol of fumaric acid.

FIG. 606 depicts the ¹H NMR of tabernanthalog monofumarate salt; 6-A2(Experiment Reference 6-Sample Reference A2) (t=10 d), acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of fumaric acid.

FIG. 607 depicts the DSC profile of tabernanthalog monofumarate salt;6-A1 (Experiment Reference 6-Sample Reference A1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 608 depicts the DSC profile of tabernanthalog monofumarate salt;6-A2 (Experiment Reference 6-Sample Reference A2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 609 depicts the TGA of tabernanthalog monofumarate salt; 6-A1(Experiment Reference 6-Sample Reference A1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 610 depicts the TGA of tabernanthalog monofumarate salt; 6-A2(Experiment Reference 6-Sample Reference A2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 611 depicts the XRPD of tabernanthalog monofumarate salt; 6-A1(Experiment Reference 6-Sample Reference A1) (t=5 d).

FIG. 612 depicts the XRPD of tabernanthalog monofumarate salt; 6-A2(Experiment Reference 6-Sample Reference A2) (t=10 d).

FIG. 613 depicts the HPLC of tabernanthalog monofumarate salt; 6-A1(Experiment Reference 6-Sample Reference A1) (t=5 d).

FIG. 614 depicts the HPLC of tabernanthalog monofumarate salt; 6-A2(Experiment Reference 6-Sample Reference A2) (t=10 d).

FIG. 615 depicts the PLM of tabernanthalog monofumarate salt; 8-A4 ofExample 5 (Experiment Reference 8-Sample Reference A4 of Example 5)(input)×2 mag, NP.

FIG. 616 depicts the PLM of tabernanthalog monofumarate salt; 8-A4 ofExample 5 (Experiment Reference 8-Sample Reference A4 of Example 5)(input)×2 mag, CP.

FIG. 617 depicts the PLM of tabernanthalog monofumarate salt; 6-A1(Experiment Reference 6-Sample Reference A1) (t=5 d)×5 mag, NP.

FIG. 618 depicts the PLM of tabernanthalog monofumarate salt; 6-A1(Experiment Reference 6-Sample Reference A1) (t=5 d)×5 mag, CP.

FIG. 619 depicts the PLM of tabernanthalog monofumarate salt; 6-A2(Experiment Reference 6-Sample Reference A2) (t=10 d)×5 mag, NP.

FIG. 620 depicts the PLM of tabernanthalog monofumarate salt; 6-A2(Experiment Reference 6-Sample Reference A2) (t=10 d)×5 mag, CP.

FIG. 621 depicts the ¹H NMR of tabernanthalog tartrate salt; 6-B1(Experiment Reference 6-Sample Reference B1) (t=5 d), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. 1.0 mol of API to 1.0 mol of L-tartaric acid, 1.0to 1.0.

Ethanol not detected.

FIG. 622 depicts the ¹H NMR of tabernanthalog tartrate salt; 6-B2(Experiment Reference 6-Sample Reference B2) (t=10 d), acquired inDMSO-d6 and calibrated to the non-deuterated solvent residual at 2.50ppm. 1.0 mol of API to 1.0 mol of L-tartaric acid.

FIG. 623 depicts the DSC profile of tabernanthalog tartrate salt; 6-B1(Experiment Reference 6-Sample Reference B1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 624 depicts the DSC profile of tabernanthalog tartrate salt; 6-B2(Experiment Reference 6-Sample Reference B2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 625 depicts the TGA of tabernanthalog tartrate salt; 6-B1(Experiment Reference 6-Sample Reference B1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 626 depicts the TGA of tabernanthalog tartrate salt; 6-B2(Experiment Reference 6-Sample Reference B2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 627 depicts the XRPD of tabernanthalog tartrate salt; 6-B1(Experiment Reference 6-Sample Reference B1) (t=5 d).

FIG. 628 depicts the XRPD of tabernanthalog tartrate salt; 6-B2(Experiment Reference 6-Sample Reference B2) (t=10 d).

FIG. 629 depicts the HPLC of tabernanthalog tartrate salt; 6-B1(Experiment Reference 6-Sample Reference B1) (t=5 d).

FIG. 630 depicts the HPLC of tabernanthalog tartrate salt; 6-B2(Experiment Reference 6-Sample Reference B2) (t=10 d).

FIG. 631 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1) (input)×2 mag, NP.

FIG. 632 depicts the PLM of tabernanthalog tartrate salt; 3-A1(Experiment Reference 3-Sample Reference A1) (input)×2 mag, CP.

FIG. 633 depicts the PLM of tabernanthalog tartrate salt; 6-B1(Experiment Reference 6-Sample Reference B1) (t=5 d)×5 mag, NP.

FIG. 634 depicts the PLM of tabernanthalog tartrate salt; 6-B1(Experiment Reference 6-Sample Reference B1) (t=5 d)×5 mag, CP.

FIG. 635 depicts the PLM of tabernanthalog tartrate salt; 6-B2(Experiment Reference 6-Sample Reference B2) (t=10 d)×5 mag, NP.

FIG. 636 depicts the PLM of tabernanthalog tartrate salt; 6-B2(Experiment Reference 6-Sample Reference B2) (t=10 d)×5 mag, CP.

FIG. 637 depicts the ¹H NMR of tabernanthalog benzoate salt; 6-C1(Experiment Reference 6-Sample Reference C1) (t=5 d), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. 1.0 mol of API to 1.0 mol of benzoic acid. Ethanolcontent 0.3% w/w.

FIG. 638 depicts the ¹H NMR of tabernanthalog benzoate salt; 6-C2(Experiment Reference 6-Sample Reference C2) (t=10 d), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. 1.0 mol of API to 1.0 mol of benzoic acid. Ethanolcontent 0.2% w/w.

FIG. 639 depicts the DSC profile of tabernanthalog benzoate salt; 6-C1(Experiment Reference 6-Sample Reference C1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 640 depicts the DSC profile of tabernanthalog benzoate salt; 6-C2(Experiment Reference 6-Sample Reference C2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 641 depicts the TGA of tabernanthalog benzoate salt; 6-C1(Experiment Reference 6-Sample Reference C1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 642 depicts the TGA of tabernanthalog benzoate salt; 6-C2(Experiment Reference 6-Sample Reference C2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 643 depicts the XRPD of tabernanthalog benzoate salt; 6-C1(Experiment Reference 6-Sample Reference C1) (t=5 d).

FIG. 644 depicts the XRPD of tabernanthalog benzoate salt; 6-C2(Experiment Reference 6-Sample Reference C2) (t=10 d).

FIG. 645 depicts the HPLC of tabernanthalog benzoate salt; 6-C1(Experiment Reference 6-Sample Reference C1) (t=5 d).

FIG. 646 depicts the HPLC of tabernanthalog benzoate salt; 6-C2(Experiment Reference 6-Sample Reference C2) (t=10 d).

FIG. 647 depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1) (input)×2 mag, NP.

FIG. 648 depicts the PLM of tabernanthalog benzoate salt; 3-B1(Experiment Reference 3-Sample Reference B1) (input)×2 mag, CP.

FIG. 649 depicts the PLM of tabernanthalog benzoate salt; 6-C1(Experiment Reference 6-Sample Reference C1) (t=5 d)×2 mag, NP.

FIG. 650 depicts the PLM of tabernanthalog benzoate salt; 6-C1(Experiment Reference 6-Sample Reference C1) (t=5 d)×2 mag, CP.

FIG. 651 depicts the PLM of tabernanthalog benzoate salt; 6-C2(Experiment Reference 6-Sample Reference C2) (t=10 d)×2 mag, NP.

FIG. 652 depicts the PLM of tabernanthalog benzoate salt; 6-C2(Experiment Reference 6-Sample Reference C2) (t=10 d)×2 mag, CP.

FIG. 653 depicts the ¹H NMR of tabernanthalog sorbate salt; 6-D1(Experiment Reference 6-Sample Reference D1) (t=5 d), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. 1.0 mol of API to 1.0 mol of sorbic acid. Ethanolcontent 0.1% w/w.

FIG. 654 depicts the ¹H NMR of tabernanthalog sorbate salt; 6-D2(Experiment Reference 6-Sample Reference D2) (t=10 d), analysis wasacquired in DMSO-d6 and calibrated to the non-deuterated solventresidual at 2.50 ppm. 1.0 mol of API to 1.0 mol of sorbic acid. Ethanolcontent 0.1% w/w.

FIG. 655 depicts the DSC profile of tabernanthalog sorbate salt; 6-D1(Experiment Reference 6-Sample Reference D1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 656 depicts the DSC profile of tabernanthalog sorbate salt; 6-D2(Experiment Reference 6-Sample Reference D2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 657 depicts the TGA of tabernanthalog sorbate salt; 6-D1(Experiment Reference 6-Sample Reference D1) (t=5 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 658 depicts the TGA of tabernanthalog sorbate salt; 6-D2(Experiment Reference 6-Sample Reference D2) (t=10 d), analysis wasacquired at a ramp rate of +10° C./minute.

FIG. 659 depicts the XRPD of tabernanthalog sorbate salt; 6-D1(Experiment Reference 6-Sample Reference D1) (t=5 d).

FIG. 660 depicts the XRPD of tabernanthalog sorbate salt; 6-D2(Experiment Reference 6-Sample Reference D2) (t=10 d).

FIG. 661 depicts the HPLC of tabernanthalog sorbate salt; 6-D1(Experiment Reference 6-Sample Reference D1) (t=5 d).

FIG. 662 depicts the HPLC of tabernanthalog sorbate salt; 6-D2(Experiment Reference 6-Sample Reference D2) (t=10 d).

FIG. 663 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1) (input)×5 mag, NP.

FIG. 664 depicts the PLM of tabernanthalog sorbate salt; 3-C1(Experiment Reference 3-Sample Reference C1) (input)×5 mag, CP.

FIG. 665 depicts the PLM of tabernanthalog sorbate salt; 6-D1(Experiment Reference 6-Sample Reference D1) (t=5 d)×2 mag, NP.

FIG. 666 depicts the PLM of tabernanthalog sorbate salt; 6-D1(Experiment Reference 6-Sample Reference D1) (t=5 d)×2 mag, CP.

FIG. 667 depicts the PLM of tabernanthalog sorbate salt; 6-D2(Experiment Reference 6-Sample Reference D2) (t=10 d)×5 mag, NP.

FIG. 668 depicts the PLM of tabernanthalog sorbate salt; 6-D2(Experiment Reference 6-Sample Reference D2) (t=10 d)×5 mag, CP.

FIG. 669 depicts the DVS of tabernanthalog monofumarate salt; 8-A4 ofExample 5 ((Experiment Reference 8-Sample Reference A4 of Example 5),kinetic plot and isotherm analysis report.

FIG. 670 depicts the DVS of tabernanthalog monofumarate salt; 8-A4 ofExample 5 ((Experiment Reference 8-Sample Reference A4 of Example 5),isothermal plot.

FIG. 671 depicts the XRPD of tabernanthalog monofumarate salt; 8-A4 ofExample 5 (Experiment Reference 8-Sample Reference A4 of Example 5)(post DVS 0 to 90% RH, top diffractogram), compared with the inputsample tabernanthalog monofumarate salt; 8-A4 of Example 5 (bottomdiffractogram).

FIG. 672 depicts the XRPD of the as-received fumarate material (ref.batch: Sample Reference 1). It was characterized as Pattern #1.

FIG. 673 depicts the XRPD profile of Pattern #6a, Form A.

FIG. 674 depicts the XRPD of the tabernanthalog fumarate sampleprepared.

FIG. 675 depicts the tabernanthalog sorbate salt.

FIG. 676 depicts the overlaid of ¹H NMR spectra of Experiment 2-SampleM2 (MEK n.d., top) and Experiment 1-Sample A2 (Form A, assay, bottom).DMSO-d₆ used as deuterated solvent. TCNB used in Experiment 1-Sample A2as internal standard.

FIG. 677 depicts the overlaid of ¹H NMR spectra of Experiment 2-SampleO2 (nitromethane n.d., top) and Experiment 1-Sample A2 (Form A, assay,bottom). DMSO-d₆ used as deuterated solvent. TCNB used in Experiment1-Sample A2 as internal standard.

FIG. 678 depicts the overlaid ¹H NMR spectra of Experiment 2-Sample S2(from water, insufficient material for KF analysis, top) and Experiment1-Sample A2 (Form A, assay, bottom). DMSO-d₆ used as deuterated solvent.TCNB used in Experiment 1-Sample A2 as internal standard.

FIG. 679 depicts the overlaid of XRPD profiles of Experiment 3-Sample R1(pattern #2, top) and Experiment 1-Sample A2 (Form A, bottom) FIG. 680depicts the overlaid of XRPD profiles of, from top to bottom, Experiment4-Sample E1 (pattern #5), Experiment 4-Sample H1 (pattern #3),Experiment 4-Sample R1 (pattern #4) and Experiment 1-Sample A2 (Form A).

FIG. 681 depicts the overlaid of XRPD profiles of Experiment 7-Sample A(neat, top) and Experiment 1-Sample A2 (Form A, bottom).

FIG. 682 depicts the overlaid of ¹H NMR spectra of Experiment 7-Sample A(top) and Experiment 1-Sample A2 (Form A, bottom). DMSO-d₆ used asdeuterated solvent.

FIG. 683 depicts the DSC profile of Experiment 7-Sample A neat.

FIG. 684 depicts the overlaid of XRPD profiles of Experiment 7-Sample B(water, top) and Experiment 1-Sample A2 (Form A, bottom).

FIG. 685 depicts the overlaid of ¹H NMR spectra of Experiment 7-Sample B(top) and Experiment 1-Sample A2 (Form A, bottom). DMSO-d₆ used asdeuterated solvent.

FIG. 686 depicts the DSC profile of Experiment 7-Sample B water.

FIG. 687 depicts the samples after 7 days. From left to right:Experiment 6-Sample A, B, C, D and E.

FIG. 688 depicts the overlaid of XRPD profiles of Tabernanthalog Sorbateat t=0: Experiment 6-Sample A1 (via evaporation from water andconsistent with pattern #1, Form B, bottom) and Experiment 1-Sample A2(Form A, top).

FIG. 689 depicts the DSC profile of Experiment 6-Sample A1 T=0.De-hydration behaviour more consistent with channel or pocket hydration;no transition was evident into Form A.

FIG. 690 depicts the overlay of ¹H NMR spectra of Tabernanthalog Sorbateat t=0: Experiment 6-Sample A1 (via evaporation from water andconsistent with pattern #1, Form B, bottom) and Experiment 1-Sample A2(Form A, top). DMSO-d₆ used as deuterated solvent.

FIG. 691 depicts the overlay of XRPD profiles of Tabernanthalog Sorbateat t=8 days: Experiment 6-Sample A1 (t=8 d) (t=8 days, Pattern changed,appeared to be reverting into Form A; middle) and Experiment 6-Sample A1(t=0, Pattern #1, Form B, top) and Tabernanthalog sorbate salt(Experiment 1-Sample A2, Form A, reference standard, bottom).

FIG. 692 depicts the DSC profile of Experiment 6-Sample A1 T=8d at t=8days. De-hydration enthalpy converted to single mode present at T-8 daysand enthalpy reduced.

FIG. 693 depicts the TGA profile of Experiment 6-Sample A1 T-8d at t=8days.

FIG. 694 depicts the overlay of, from bottom to top, XRPD profiles ofTabernanthalog Sorbate: Experiment 1-Sample A2 (Form A), Experiment6-Sample A1 (t=0, Pattern #1, Form B), Experiment 6-Sample A1 (t=8d)(t=8 days, Pattern changed, appeared to be reverting into Form A) andExperiment 6-Sample A1 after DSC (DSC up to 80° C., congruent with FormA).

FIG. 695 depicts the DSC profile of Experiment 6-Sample A1 Rep.

FIG. 696 depicts the PLM of Experiment 6-Sample A1 (normal polarisation,×2 magnification.).

FIG. 697 depicts the overlay of, from top to bottom, ¹H NMR spectra ofTabernanthalog Sorbate samples: Experiment 1-Sample A2 (Form A),Experiment 8-Sample A1 (wet pellet, Pattern #1, Form B), Experiment8-Sample A2 (dried under N₂ purge, different from Pattern #1, Form B andForm A) and Experiment 5-Sample Q1 (Pattern #1, Form B crystallised fromwater).

FIG. 698 depicts the overlay of, from top to bottom, ¹H NMR spectra ofTabernanthalog Sorbate samples: Experiment 1-Sample A2 (Form A),Experiment 8-Sample B1 (wet pellet, Form A), Experiment 8-Sample B2(dried under N₂ purge, Form A) and Experiment 5-Sample G1 (Pattern #6,crystallised from EtOAc/heptane).

FIG. 698A depicts the summary of results.

FIG. 699 depicts the DVS data of Experiment 1-Sample A2.

FIG. 700 depicts the overlay of XRPD profiles of Experiment 11-Sample A1Post DVS (bottom) and Experiment 1-Sample A2 (top).

FIG. 701 depicts the DSC profile of Experiment 11-Sample A1 post DVS,m.p. of specimen at 80% RH was consistent with Form A.

FIG. 702 depicts the overlay of XRPD profiles of Experiment 11-Sample A1post DVS (0 to 90 RH, bottom) and Experiment 1-Sample A2 (top).

FIG. 703 depicts the DSC profile of Experiment 11-Sample A1 post DVS (0%to 90% RH).

FIG. 704 depicts the overlay of XRPD profiles of the various batchesthat resemble Form A.

FIG. 705 depicts the asymmetric unit of Experiment 11-Sample A1 (Form A)at 100K with thermal ellipsoids drawn at 50% probability. Both disordercomponents shown.

FIG. 706 depicts the hydrogen bonding network of Tabernanthalog sorbatesalt (Experiment 11-Sample A1, Form A).

FIG. 707 depicts the hydrogen bonding network of Tabernanthalog sorbatesalt (Experiment 11-Sample A1, Form A).

FIG. 708 depicts the calculated hydrogen bond lengths of Tabernanthalogsorbate salt (Experiment 11-Sample A1, Form A).

FIG. 709 depicts the simulated powder diffraction pattern ofTabernanthalog sorbate salt (Experiment 11-Sample A1, Form A).

FIG. 710 depicts the XRPD diffractogram overlay of simulated powderdiffraction pattern of Tabernanthalog sorbate salt (bottom, Experiment11-Sample A1, Form A) and Experiment 11-Sample A1 (top, Form A,experimental).

FIG. 711 depicts the asymmetric unit of Tabernanthalog sorbate salt·H₂O(Experiment 12-Sample A2) at 100K with thermal ellipsoids drawn at 50%probability. Both disorder components shown.

FIG. 712 depicts the asymmetric unit of Tabernanthalog sorbate salt·H₂O(Experiment 12-Sample A2) at 100K with thermal ellipsoids drawn at 50%probability. Both disorder components shown.

FIG. 713 depicts the hydrogen bonding network of Tabernanthalog sorbatesalt·H₂O (Experiment 12-Sample A2).

FIG. 714 depicts the calculated hydrogen bond lengths of Tabernanthalogsorbate salt·H₂O (Experiment 12-Sample A2).

FIG. 715 depicts the void space analysis of Tabernanthalog sorbatesalt·H₂O (Experiment 12-Sample A2).

FIG. 716 depicts the packing of Tabernanthalog sorbate salt·H₂O(Experiment 12-Sample A2).

FIG. 717 depicts the simulated powder diffraction pattern ofTabernanthalog sorbate salt·H₂O (Experiment 12-Sample A2).

FIG. 718 depicts the XRPD diffractogram overlay of simulated powderdiffraction pattern of Tabernanthalog sorbate salt·H₂O (top, Experiment12-Sample A2, hydrate) and Experiment 12-Sample A2 (bottom,experimental).

FIG. 719 depicts the ¹H NMR spectrum of Experiment 1-Sample A2 inDMSO-d₆ used as deuterated solvent.

FIG. 720 depicts the Q NMR assay of Experiment 1-Sample A2 in DMSO-d₆used as deuterated solvent. 99.9% w/w assay.

FIG. 721 depicts the ¹H NMR spectrum of Experiment 6-Sample A1. DMSO-d₆used as deuterated solvent.

FIG. 722 depicts the DSC profile of Experiment 6-Sample A1, t=0.

FIG. 723 depicts the DSC profile of Experiment 6-Sample A1, t=8 days.

FIG. 724 depicts the DSC profile of Experiment 6-Sample A1 Rep from 20to 80° C.

FIG. 725 depicts the TGA profile of Experiment 6-Sample A1 t=0 days.

FIG. 726 depicts the TGA profile of Experiment 6-Sample A1 t=8 days.

FIG. 727 depicts the XRPD profile of Experiment 2-Sample S1.

FIG. 728 depicts the XRPD profile of Experiment 6-Sample A1.

FIG. 728A depicts the PLM of Experiment 12-Sample A2.

FIG. 729 depicts the ¹H NMR spectrum of Experiment 10-Sample A2.

FIG. 730 depicts the DSC profile of Experiment 10-Sample A2.

FIG. 731 depicts the TGA profile of Experiment 10-Sample A2.

FIG. 732 depicts the HPLC profile of Experiment 10-Sample A2.

FIG. 733 depicts the PLM of Experiment 10-Sample A2.

FIG. 734 depicts the PLM of Experiment 3-Sample R1 (cross-polarised).

FIG. 735 depicts the XRPD profile of Experiment 3-Sample R1.

FIG. 736 depicts the XRPD profile of Experiment 10-Sample A2.

FIG. 737 depicts the XRPD profile of Experiment 4-Sample H1.

FIG. 738 depicts the XRPD profile of Experiment 5-Sample R1.

FIG. 739 depicts the XRPD profile of Experiment 4-Sample E1.

FIG. 740 depicts the XRPD profile of Experiment 5-Sample G1.

FIG. 741 depicts the ¹H NMR spectrum of Experiment 13-Sample C1. DMSO-d₆used as deuterated solvent.

FIG. 742 depicts the DSC profile of Experiment 13-Sample C1.

FIG. 743 depicts the TGA profile of Experiment 13-Sample C1.

FIG. 744 depicts the HPLC profile of Experiment 13-Sample C1.

FIG. 755 depicts the polarized light microscopy of Experiment 13-SampleC1.

FIG. 756 depicts the XRPD profile of Experiment 13-Sample C1.

FIG. 757 depicts the DSC profile of Experiment 7-Sample A Neat.

FIG. 758 depicts the XRPD profile of Experiment 7-Sample A Neatpulverization.

FIG. 759 depicts the DSC profile of Experiment 7-Sample B water.

FIG. 760 depicts the XRPD profile of Experiment 7-Sample B water.

FIG. 761 depicts the ¹H NMR spectrum of Experiment 8-Sample A2. DMSO-d₆used as deuterated solvent. The chemical composition appears differentchemical composition and is attributed to reaction with ethyl formate.Solvent exchange had occurred during oven-drying.

FIG. 762 depicts the DSC profile of Experiment 8-Sample A2.

FIG. 763 depicts the TGA profile of Experiment 8-Sample A2.

FIG. 764 depicts the PLM of Experiment 8-Sample A2.

FIG. 765 depicts the XRPD profile of Experiment 8-Sample A2.

FIG. 766 depicts the ¹H NMR spectrum of Experiment 8-Sample B2. DMSO-d₆used as deuterated solvent.

FIG. 767 depicts the DSC profile of Experiment 8-Sample B2.

FIG. 768 depicts the TGA profile of Experiment 8-Sample B2.

FIG. 769 depicts the XRPD profile of Experiment 8-Sample B2.

FIG. 770 depicts the XRPD profile of Experiment 12-Sample A2.

FIG. 771 depicts the Overlaid of XRPD profiles of Tabernanthalog sorbatesalt samples: Experiment 6-Sample B1 (via evaporation frommethanol/acetone consistent with Pattern #1>Form A>unk, top), Experiment6-Sample A1 (via evaporation from water, Pattern #1, Form B, bottom) andExperiment 1-Sample A2 (Form A, middle).

FIG. 772 depicts the DSC profile of Experiment 6-Sample B1.Predominantly Form A.

FIG. 773 depicts the DSC profile of Experiment 6-Sample C1(Methanol/acetonitrile) Form A.

FIG. 774 depicts the DSC profile of Experiment 6-Sample D1(Methanol/THF) Form A.

FIG. 775 depicts the DSC profile of Experiment 6-Sample E1(Methanol/DCM) Form A.

FIG. 776 depicts the TGA profile of Experiment 6-Sample C1(Methanol/acetonitrile) Form A.

FIG. 777 depicts the TGA profile of Experiment 6-Sample C1 repeated(Methanol/acetonitrile) Form A. Repeated, positive pressure event gaveTGA>unity.

FIG. 778 depicts the TGA profile of Experiment 6-Sample D1(Methanol/THF) Form A.

FIG. 779 depicts the TGA profile of Experiment 6-Sample E1(Methanol/DCM) Form A.

FIG. 780 depicts the overlay of XRPD profiles of Experiment 1-Sample A2(form A, top) and Experiment 6-Sample C1 (methanol/acetonitrile,bottom).

FIG. 781 depicts the overlay of XRPD profiles of Experiment 1-Sample A2(form A, top) and Experiment 6-Sample D1 (methanol/THF, bottom).

FIG. 782 depicts the overlay of XRPD profiles of Experiment 1-Sample A2(form A, top) and Experiment 6-Sample E1 (methanol/DCM, bottom).

FIG. 783 depicts the overlay of, from top to bottom, XRPD of Experiment1-Sample A2 (Form A), Experiment 9-Sample A1 (wet pellet, Pattern #2),Experiment 9-Sample A2 (dried under N2 purge, Pattern #2) and Experiment3-Sample R1 (wet pellet, Pattern #2).

FIG. 784 depicts the DSC profile of Experiment 9-Sample A2 (t=0).

FIG. 785 depicts the DSC profile of Experiment 9-Sample A2 (t=4 days).

FIG. 786 depicts the overlay of, from top to bottom, XRPD of Experiment1-Sample A2 (Form A), Experiment 9-Sample B1 (wet pellet, Pattern #2),Experiment 9-Sample B2 (dried under N2 purge, Pattern #2) and Experiment4-Sample R1 (wet pellet, Pattern #4).

FIG. 787 depicts the DSC profile of Experiment 9-Sample B2.

FIG. 788 depicts the TGA profile of Experiment 9-Sample B2 (T=0).

FIG. 789 depicts the TGA profile of Experiment 9-Sample B2 (t=7 days).

FIG. 790 depicts the overlay of XRPD of, from top to bottom, Experiment1-Sample A2 (Form A), Experiment 9-Sample C1 (wet pellet, Form A),Experiment 9-Sample C2 (dried under N2 purge, Form A) and Experiment4-Sample H1 (wet pellet, Pattern #3).

FIG. 791 depicts the overlay of, from top to bottom, XRPD of Experiment1-Sample A2 (Form A), Experiment 9-Sample D1 (wet pellet, Pattern #5),Experiment 9-Sample D2 (dried under N2 purge, Pattern #5) and Experiment4-Sample E1 (wet pellet, Pattern #5).

FIG. 792 depicts the DSC profile of Experiment 10-Sample A2.

FIG. 793 depicts the TGA profile of Experiment 10-Sample A2 (t=10 days).

FIG. 794 depicts the DSC profile of Experiment 10-Sample B2 (t=10 days).

FIG. 795 depicts the TGA profile of Experiment 10-Sample B2 (t=10 days).

FIG. 796 depicts the PLM of Experiment 10-Sample A2 and B2 (t=10 days).

FIG. 797 depicts the overlay of, from top to bottom, XRPD of Experiment1-Sample A2 (Form A), Experiment 10-Sample A1 (5 days, open vial Pattern#2), Experiment 10-Sample A2 (10 days, open vial, Pattern #2),Experiment 10-Sample B1 (5 days, double-bagged vial, Form A) andExperiment 10-Sample B2 (10 days, double-bagged vial, Pattern #2).

FIG. 798 depicts the overlay of ¹H NMR spectra of Experiment 10-SampleA2 (t=10 days, open vial, top) and Experiment 1-Sample A2 (Q NMR assay,bottom). DMSO-d₆ used as deuterated solvent and TCNB used as internalstandard in Experiment 1-Sample A2.

FIG. 799 depicts the overlay of ¹H NMR spectra of Experiment 10-SampleB2 (t=10 days, double-bagged vial, top) and Experiment 1-Sample A2 (QNMR assay, bottom). DMSO-d₆ used as deuterated solvent and TCNB used asinternal standard in Experiment 1-Sample A2.

FIG. 800 depicts the HPLC profile of Experiment 1-Sample A2 input.

FIG. 801 depicts the HPLC profile of Experiment 10-Sample A2 t=10 days,open vial.

FIG. 802 depicts the HPLC profile of Experiment 10-Sample B2 t=10 days,open vial.

FIG. 803 depicts the DSC profile of A127-076-A1.

FIG. 804 depicts the TGA profile of A127-076-A1.

FIG. 805 depicts the overlay of XRPD profiles of Experiment 13-Sample C1(initial 1 g batch, top) and Experiment 11-Sample A1 (re-prep, bottom).

FIG. 806 depicts the ¹H NMR spectrum of Experiment 11-Sample A1. DMSO-d₆used as deuterated solvent and TCNB used as internal standard. 99.5% w/wassay. 0.1% w/w ethanol content 1 to 1 ratio of API to sorbic acid.

FIG. 807 depicts the PLM of Experiment 11-Sample -A1.

FIG. 808 depicts the DVS isotherm plot of Experiment 1-Sample A2.

FIG. 809 depicts the overlay of XRPD profiles of Experiment 1-Sample A2(form A, top) and Experiment 1-Sample A2_post-DVS (form A, bottom).

FIG. 810 depicts the SC-XRPD Characterization of Tabernanthalog SorbateForm A.

FIG. 811 depicts the SC-XRPD Characterization of Tabernanthalog SorbateHydrate.

FIG. 812 depicts the overlay of, from bottom to top, XRPD profiles ofTabernanthalog·Sorbate, Input, Form A, Experiment 6-Sample A1 (30 Hz, 2h), Experiment 6-Sample A2 (30 Hz, 5.5 h), and Experiment 6-Sample A3(30 Hz, 1 h, Tetradecafluorohexane).

FIG. 813 depicts the overlay of XRPD profiles of, from bottom to top,Experiment 3-Sample C2 (Tabernanthalog·Sorbate, Form A), Experiment3-Sample C1 (Tabernanthalog·Sorbate, Input, Pattern #7) and A1270-076-A1(Tabernanthalog·Sorbate, Form A).

FIG. 814 depicts the ¹H NMR spectrum of Experiment 1-Sample D1(Tabernanthalog·Sorbate, Amorphous) in deuterated DMSO-d₆ and calibratedto the non-deuterated solvent residual of 2.50 ppm.

FIG. 815 depicts the XRPD profile of Experiment 1-Sample D1(Tabernanthalog·Sorbate, amorphous).

FIG. 816 depicts the LC-MS profile of Experiment 1-Sample E1(Tabernanthalog·Sorbate, Amorphous), Spectra (top) M/Z (bottom).

FIG. 817 depicts the ¹H NMR spectrum of Experiment 3-Sample A2(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7) in deuterated DMSO-d₆,calibrated to the non-deuterated solvent residual.

FIG. 818 depicts the ¹⁹F NMR spectrum of Experiment 3-Sample A2(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7) in deuterated DMSO-d_(6.)

FIG. 819 depicts the ¹⁹F NMR spectrum of Experiment 3-Sample A2(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7) versus internal standardα,α,α-trifluorotoluene in deuterated DMSO-d_(6.)

FIG. 820 depicts the XRPD profile of Experiment 3-Sample A2(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7).

FIG. 821 depicts the DSC profile of Experiment 3-Sample A2(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7).

FIG. 822 depicts TGA profile of Experiment 3-Sample A2(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7).

FIG. 823 depicts the ¹H NMR spectrum of Experiment 2-Sample D1(Tabernanthalog·Monofumarate, Amorphous) in deuterated DMSO-d_(6.)

FIG. 824 depicts the XRPD profile of Experiment 2-Sample D1(Tabernanthalog·Monofumarate).

FIG. 825 depicts the LC-MS profile of Experiment 2-Sample E1(Tabernanthalog·Monofumarate, Amorphous), Spectra (top) M/Z (bottom).

FIG. 826 depicts the XRPD profile of Experiment 4-Sample A1(Tabernanthalog·Sorbate, Form A).

FIG. 827 depicts the XRPD profile of Experiment 4-Sample A2(Tabernanthalog·Sorbate, Form A).

FIG. 828 depicts the XRPD profile of Experiment 4-Sample A3(Tabernanthalog·Sorbate, Form A).

FIG. 829 depicts the XRPD profile of Experiment 4-Sample A4(Tabernanthalog·Sorbate, Form A).

FIG. 830 depicts the XRPD profile of Experiment 4-Sample B1(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7).

FIG. 831 depicts the XRPD profile of Experiment 4-Sample B2(Tabernanthalog·Sorbate).

FIG. 832 depicts the XRPD profile of Experiment 4-Sample B3(Tabernanthalog·Sorbate, Pattern #7).

FIG. 833 depicts the XRPD profile of Experiment 4-Sample C1(Tabernanthalog·Sorbate, Form A).

FIG. 834 depicts the XRPD profile of Experiment 4-Sample D1(Tabernanthalog·Sorbate, Form A).

FIG. 835 depicts the XRPD profile of Experiment 4-Sample D2(Tabernanthalog·Sorbate, Form A).

FIG. 836 depicts the XRPD profile of Experiment 4-Sample E1(Tabernanthalog·Sorbate, Form A).

FIG. 837 depicts the XRPD profile of Experiment 5-Sample A1(Tabernanthalog·Monofumarate, Pattern #1).

FIG. 838 depicts the XRPD profile of Experiment 5-Sample A2(Tabernanthalog·Monofumarate, Pattern #11).

FIG. 839 depicts the XRPD profile of Experiment 5-Sample A3(Tabernanthalog·Monofumarate, Pattern #3).

FIG. 840 depicts the XRPD profile of Experiment 6-Sample A1(Tabernanthalog·Sorbate, Form A).

FIG. 841 depicts the XRPD profile of Experiment 6-Sample A2(Tabernanthalog·Sorbate, Form A).

FIG. 842 depicts the XRPD profile of Experiment 6-Sample A3(Tabernanthalog·Sorbate, Form A).

FIG. 843 depicts the XRPD profile of Experiment 1-Sample D1(Tabernanthalog·Sorbate, amorphous).

FIG. 844 depicts the XRPD profile of Experiment 1-Sample D2(Tabernanthalog·Sorbate, Form A). Experiment 1-Sample D1 left standingovernight in ambient conditions to yield crystalline material(Experiment 1-Sample D2).

FIG. 845 depicts the XRPD profile of Experiment 1-Sample E1(Tabernanthalog·Sorbate, amorphous).

FIG. 846 depicts the XRPD profile of Experiment 2-Sample D1(Tabernanthalog·Monofumarate, amorphous).

FIG. 847 depicts the XRPD profile of Experiment 2-Sample E1(Tabernanthalog·Monofumarate).

FIG. 848 depicts an overlay of ¹H NMR spectra of Experiment 1-Sample D1(Tabernanthalog·Sorbate, Amorphous, DMSO-d₆ upper spectrum, top) andA1270-076-A1 (Tabernanthalog·Sorbate, Form A, DMSO-d₆, Internalstandard: TCNB, lower spectrum, bottom).

FIG. 849 depicts an overlay of ¹H NMR spectra of Experiment 2-Sample D1(Tabernanthalog·Monofumarate, amorphous, DMSO-d₆, lower spectrum, bottomand Tabernanthalog·Monofumarate (Tabernanthalog·Monofumarate, Pattern#1, DMSO-d₆ top).

FIG. 850 depicts extracted DSC profiles of Experiment 1-SampleA1(Tabernanthalog·Sorbate) cycle 1 and cycle 2.

FIG. 851 depicts the complete thermocycle DSC profile of Experiment1-Sample B1 (Tabernanthalog·Sorbate) (heat flow vs time).

FIG. 852 depicts the extracted DSC profiles of Experiment 2-Sample A1(Tabernanthalog·Monofumarate, cycle 1 top, cycle 2 bottom).

FIG. 853 depicts the thermocycle DSC profile of Experiment 2-Sample B1(Tabernanthalog·Monofumarate, heat flow vs time).

FIG. 854 depicts the thermocycle TGA profile of Experiment 1-Sample C1(Tabernanthalog·Sorbate, mass loss vs time).

FIG. 855 depicts the thermocycle TGA profile of Experiment 2-Sample C1(Tabernanthalog·Monofumarate, mass loss vs time).

FIG. 856 depicts the LC-MS profile of Experiment 1-Sample E1(Tabernanthalog·Sorbate, Amorphous), Spectra (top) m/z (bottom).

FIG. 857 depicts the LC-MS profile of Experiment 2-Sample E1(Tabernanthalog·Monofumarate, amorphous), spectrum (top) m/z (bottom).

FIG. 858 depicts the XRPD profile of Experiment 3-Sample A1(Tabernanthalog·Sorbate, Pattern #7).

FIG. 859 depicts the XRPD profile of Experiment 3-Sample B1(Tabernanthalog·Sorbate, Pattern #7) 20° C., 75% RH, 5 d.

FIG. 860 depicts the XRPD profile of Experiment 3-Sample C1(Tabernanthalog·Sorbate, Pattern #7). 40° C., 75% RH, 5 d.

FIG. 861 depicts the XRPD profile of Experiment 3-Sample C2(Tabernanthalog·Sorbate, Form A), Heated to 100° C. prior to XRPD.

FIG. 862 depicts the overlay of ¹H NMR spectra of A1270-076-A1(Tabernanthalog·Sorbate, Form A, Internal standard: TCNB DMSO-d₆, upperspectrum, top) and Experiment 3-Sample A2(Tabernanthalog·Sorbate·hemiHFIPA, Pattern #7, DMSO-d₆ bottom, lowerspectrum).

FIG. 863 depicts the DSC profile of Experiment 3-Sample B1(Tabernanthalog·Sorbate·hemiHFIPA, Pattern #7).

FIG. 864 depicts the TGA profile of Experiment 3-Sample B1(Tabernanthalog·Sorbate·hemiHFIPA, Pattern #7).

FIG. 865 depicts the TGA profile of Experiment 3-Sample C1(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7).

FIG. 866 depicts the TGA Profile of Experiment 3-Sample C2(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7).

FIG. 867 depicts the microscope image of Experiment 3-Sample A1(Tabernanthalog·Sorbate·HemiHFIPA, Pattern #7) (10× lens).

FIG. 868 depicts the molecular representation of Tabernanthalog·Native.

FIG. 869 depicts the molecular representation of Tabernanthalog·Nativewith protons annotated.

FIG. 870 depicts the LC-MS details for Experiment 1-Sample E1(Tabernanthalog·Sorbate, amorphous).

FIG. 871 depicts the LC-MS profile of Experiment 1-Sample E1(Tabernanthalog·Sorbate, amorphous, API=2.589 min, Sorbic acid=2.653min).

FIG. 872 depicts the LC-MS details for Sorbic Acid.

FIG. 873 depicts the LC-MS profile of Sorbic acid=2.61 min.

FIG. 874 depicts the LC-MS profile of Experiment 2-Sample E1(Tabernanthalog·Monofumarate, amorphous).

FIG. 875 depicts the LC-MS profile of Experiment 2-Sample E1 (Fumaricacid=˜0.3 min, API=2.52 min).

DETAILED DESCRIPTION I. Definitions

The following explanations of terms and methods are provided to betterdescribe the present disclosure and to guide those of ordinary skill inthe art in the practice of the present disclosure. The singular forms“a,” “an,” and “the” refer to one or more than one, unless the contextclearly dictates otherwise. The term “or” refers to a single element ofstated alternative elements or a combination of two or more elements,unless the context clearly indicates otherwise. As used herein,“comprises” means “includes.” Thus, “comprising A or B,” means“including A, B, or A and B,” without excluding additional elements.

All references, including patents and patent applications cited herein,are incorporated by reference in their entirety, unless otherwisespecified.

Unless otherwise indicated, all numbers expressing quantities ofcomponents, molecular weights, percentages, temperatures, times, and soforth, as used in the specification or claims, are to be understood asbeing modified by the term “about.” Accordingly, unless otherwiseindicated, implicitly or explicitly, the numerical parameters set forthare approximations that may depend on the desired properties soughtand/or limits of detection under standard test conditions/methods. Whendirectly and explicitly distinguishing embodiments from discussed priorart, the embodiment numbers are not approximates unless the word “about”is expressly recited.

When used in the context of XRPD signal values, the term “about” canindicate a peak value±0.20, ±0.15, ±0.10, ±0.05, or 0.01°2θ. In someembodiments, when used in the context of XRPD signal values “about” canindicate a peak value at substantially exactly the disclosed peak value.

The terms “XRPD peak”, “XRPD signal” and “XRPD peak/signal” are usedinterchangeably.

Unless explained otherwise, all technical and scientific terms usedherein have the same meaning as commonly understood by one of ordinaryskill in the art to which this disclosure pertains.

Although methods and materials similar or equivalent to those describedherein can be used in the practice or testing of the present disclosure,suitable methods and materials are described below. The materials,methods, and examples are illustrative only and not intended to belimiting.

“Administering” refers to any suitable mode of administration,including, oral administration, administration as a suppository, topicalcontact, parenteral, intravenous, intraperitoneal, intramuscular,intralesional, intranasal or subcutaneous administration, intrathecaladministration, or the implantation of a slow-release device e.g., amini-osmotic pump, to the subject.

“Tabernanthalog” refers to the compound

“Tabernanthalog fumarate” or “Tabernanthalog monofumarate” refers to thefumaric acid salt of tabernanthalog

“Tabernanthalog hemifumarate” refers to the hemifumaric acid salt oftabernanthalog

“Subject” refers to an animal, such as a mammal, including, but notlimited to, primates (e.g., humans), cows, sheep, goats, horses, dogs,cats, rabbits, rats, mice and the like. In certain embodiments, thesubject is a human subject.

“Therapeutically effective amount” or “therapeutically sufficientamount” or “effective or sufficient amount” refers to a dose thatproduces therapeutic effects for which it is administered. The exactdose will depend on the purpose of the treatment, and will beascertainable by one skilled in the art using known techniques (see,e.g., Lieberman, Pharmaceutical Dosage Forms (vols. 1-3, 1992); Lloyd,The Art, Science and Technology of Pharmaceutical Compounding (1999);Pickar, Dosage Calculations (1999); and Remington: The Science andPractice of Pharmacy, 20th Edition, 2003, Gennaro, Ed., Lippincott,Williams & Wilkins). In sensitized cells, the therapeutically effectivedose can often be lower than the conventional therapeutically effectivedose for non-sensitized cells.

“Neuronal plasticity” refers to the ability of the brain to change itsstructure and/or function continuously throughout a subject's life.Examples of the changes to the brain include, but are not limited to,the ability to adapt or respond to internal and/or external stimuli,such as due to an injury, and the ability to produce new neurites,dendritic spines, and synapses.

“Brain disorder” refers to a neurological disorder which affects thebrain's structure and function. Brain disorders can include, but are notlimited to, Alzheimer's, Parkinson's disease, psychological disorder,depression, treatment resistant depression, addiction, anxiety,post-traumatic stress disorder, suicidal ideation, major depressivedisorder, bipolar disorder, schizophrenia, stroke, traumatic braininjury, and substance use disorder.

“Combination therapy” refers to a method of treating a disease ordisorder, wherein two or more different pharmaceutical agents areadministered in overlapping regimens so that the subject issimultaneously exposed to both agents. For example, the compounds of theinvention can be used in combination with other pharmaceutically activecompounds. The compounds of the invention can be administeredsimultaneously (as a single preparation or separate preparation) orsequentially to the other drug therapy. In general, a combinationtherapy envisions administration of two or more drugs during a singlecycle or course of therapy.

“Neurotrophic factors” refers to a family of soluble peptides orproteins which support the survival, growth, and differentiation ofdeveloping and mature neurons.

“Modulate” or “modulating” or “modulation” refers to an increase ordecrease in the amount, quality, or effect of a particular activity,function or molecule. By way of illustration and not limitation,agonists, partial agonists, antagonists, and allosteric modulators(e.g., a positive allosteric modulator) of a G protein-coupled receptor(e.g., 5HT_(2A)) are modulators of the receptor.

“Agonism” refers to the activation of a receptor or enzyme by amodulator, or agonist, to produce a biological response.

“Agonist” refers to a modulator that binds to a receptor or enzyme andactivates the receptor to produce a biological response. By way ofexample only, “5HT_(2A) agonist” can be used to refer to a compound thatexhibits an EC₅₀ with respect to 5HT_(2A) activity of no more than about100 mM. In some embodiments, the term “agonist” includes full agonistsor partial agonists. “Full agonist” refers to a modulator that binds toand activates a receptor with the maximum response that an agonist canelicit at the receptor. “Partial agonist” refers to a modulator thatbinds to and activates a given receptor, but has partial efficacy, thatis, less than the maximal response, at the receptor relative to a fullagonist.

“Positive allosteric modulator” refers to a modulator that binds to asite distinct from the orthosteric binding site and enhances oramplifies the effect of an agonist.

“Antagonism” refers to the inactivation of a receptor or enzyme by amodulator, or antagonist. Antagonism of a receptor, for example, is whena molecule binds to the receptor and does not allow activity to occur.

“Antagonist” or “neutral antagonist” refers to a modulator that binds toa receptor or enzyme and blocks a biological response. An antagonist hasno activity in the absence of an agonist or inverse agonist but canblock the activity of either, causing no change in the biologicalresponse.

“Composition” refers to a product comprising the specified ingredientsin the specified amounts, as well as any product, which results,directly or indirectly, from combination of the specified ingredients inthe specified amounts. By “pharmaceutically acceptable” it is meant thecarrier, diluent or excipient must be compatible with the otheringredients of the formulation.

“Pharmaceutically acceptable excipient” refers to a substance that aidsthe administration of an active agent to and absorption by a subject.Pharmaceutical excipients useful in the present invention include, butare not limited to, binders, fillers, disintegrants, lubricants,coatings, sweeteners, flavors and colors. One of skill in the art willrecognize that other pharmaceutical excipients are useful in the presentinvention.

The terms “powder X-ray diffraction pattern”, “PXRD pattern”, “X-raypowder diffraction pattern”, and “XRPD pattern” are used interchangeablyand refer to the experimentally observed diffractogram or parametersderived therefrom. Powder X-ray diffraction patterns are typicallycharacterized by peak position (abscissa) and peak intensities(ordinate). The term “peak intensities” refers to relative signalintensities within a given X-ray diffraction pattern. Factors which canaffect the relative peak intensities are sample thickness and preferredorientation (i.e., the crystalline particles are not distributedrandomly). The term “peak positions” as used herein refers to X-rayreflection positions as measured and observed in powder X-raydiffraction experiments. Peak positions are directly related to thedimensions of the unit cell. The peaks, identified by their respectivepeak positions, are extracted from the diffraction patterns for thevarious polymorphic forms of salts of tabernanthalog.

The term “2 theta value”, “20” or “2 θ” refers to the peak position indegrees based on the experimental setup of the X-ray diffractionexperiment and is a common abscissa unit in diffraction patterns. Ingeneral, the experimental setup requires that if a reflection isdiffracted when the incoming beam forms an angle theta (θ) with acertain lattice plane, the reflected beam is recorded at an angle 2theta (2θ). It should be understood that reference herein to specific 2θvalues for a specific polymorphic form is intended to mean the 2θ values(in degrees) as measured using the X-ray diffraction experimentalconditions as described herein.

“Preferred orientation effects” refer to variable peak intensities orrelative intensity differences between different PXRD measurements ofthe same samples that can be due to the orientation of the particles.Without wishing to be bound by theory, in PXRD it can be desirable tohave a sample in which particles are oriented randomly (e.g., a powder).However, it can be difficult or in some cases impossible to achievetruly random particle orientations in practice. As particle sizeincreases, the randomness of particle orientation can decrease, leadingto increased challenges with achieving a preferred orientation. Withoutwishing to be bound by theory, a smaller particle size can reducetechnical challenges associated with preferred orientation and allow formore accurate representation of peaks. However, one of skill in the artwill understand how to reduce or mitigate preferred orientation effectsand will recognize preferred orientation effects that can exist evenbetween two different measurements of the same sample. For instance, insome embodiments, differences in resolution or relative peak intensitiescan be attributed to preferred orientation effects.

As used herein, the term “substantially pure” with reference to aparticular salt or solid form (or to a mixture of two or more salts) ofa compound indicates the salt or solid form (or a mixture) includes lessthan 10%, less than 5%, less than 3%, less than 1%, less than 0.5%, lessthan 0.2%, or less than 0.1% by weight of impurities, including othersalt or solid forms of the compound. Such purity may be determined, forexample, by powder X-ray diffraction.

As used herein, the term “polymorph” or “salt form” refers to differentcrystalline forms of the same compound and other solid state molecularforms including pseudo-polymorphs, such as hydrates (e.g., bound waterpresent in the crystalline structure) and solvates (e.g., bound solventsother than water) of the same compound. Different crystalline polymorphshave different crystal structures due to a different packing of themolecules in the lattice. This results in a different crystal symmetryand/or unit cell parameters which directly influences its physicalproperties such as the X-ray diffraction characteristics of crystals orpowders. A different polymorph, for example, will in general diffract ata different set of angles and will give different values for theintensities. Therefore, X-ray powder diffraction can be used to identifydifferent polymorphs, or a solid form that comprises more than onepolymorph, in a reproducible and reliable way (S. Byrn et al,Pharmaceutical Solids: A Strategic Approach to RegulatoryConsiderations, Pharmaceutical research, Vol. 12, No. 7, p. 945-954,1995; J. K. Haleblian and W. McCrone, Pharmaceutical Applications ofPolymorphism, Journal of Pharmaceutical Sciences, Vol. 58, No. 8, p. 911-929, 1969).

The term “tabernanthalog·salt” refer to the salt of tabernanthalog. Thesalt is selected from the group consisting of galactarate (mucate),naphthalene-1,5-disulfonate, citrate, sulfate, d-glucuronate,ethane-1,2-disulfonate, lactobionate, p-toluenesulfonate,D-glucoheptonate, thiocyanate, (−)-L-pyroglutamate, methanesulfonate,L-malate, dodecylsulfate, hippurate, naphthalene-2-sulfonate,D-gluconate, benzenesulfonate, D,L-lactate, oxalate, oleate,glycerophosphate, succinate, ethanesulfonate, glutarate, L-aspartate,cinnamate, maleate, adipate, phosphate, sebacate, isethionate,(+)-camphorate, glutamate, acetate, sorbate, tartrate, benzoate,maleate, fumarate, and combinations thereof.

Crystalline polymorphic forms are of interest to the pharmaceuticalindustry and especially to those involved in the development of suitabledosage forms. If the polymorphic form is not held constant duringclinical or stability studies, the exact dosage form used or studied maynot be comparable from one lot to another. It is also desirable to haveprocesses for producing a compound with the selected polymorphic form inhigh purity when the compound is used in clinical studies or commercialproducts since impurities present may produce undesired toxicologicaleffects. Certain polymorphic forms may exhibit enhanced thermodynamicstability or may be more readily manufactured in high purity in largequantities, and thus are more suitable for inclusion in pharmaceuticalformulations. Certain polymorphs may display other advantageous physicalproperties such as lack of hygroscopic tendencies, improved solubility,and enhanced rates of dissolution due to different lattice energies.

The term “amorphous” refers to any solid substance which (i) lacks orderin three dimensions, or (ii) exhibits order in less than threedimensions, order only over short distances (e.g., less than 10 A), orboth. Thus, amorphous substances include partially crystalline materialsand crystalline mesophases with, e.g., one- or two-dimensionaltranslational order (liquid crystals), orientational disorder(orientationally disordered crystals), or conformational disorder(conformationally disordered crystals). Amorphous solids may becharacterized by known techniques, including powder X-ray diffraction(PXRD) crystallography, solid state nuclear magnet resonance (ssNMR)spectroscopy, differential scanning calorimetry (DSC), or somecombination of these techniques. Amorphous solids give diffuse PXRDpatterns, typically comprised of one or two broad peaks (i.e., peakshaving base widths of about 5°2θ or greater).

The term “crystalline” refers to any solid substance exhibitingthree-dimensional order, which in contrast to an amorphous solidsubstance, gives a distinctive PXRD pattern with sharply defined peaks.

The term “ambient temperature” refers to a temperature conditiontypically encountered in a laboratory setting. This includes theapproximate temperature range of about 20 to about 30° C.

The term “detectable amount” refers to an amount or amount per unitvolume that can be detected using conventional techniques, such as X-raypowder diffraction, differential scanning calorimetry, HPLC, FourierTransform Infrared Spectroscopy (FT-IR), Raman spectroscopy, and thelike.

The term “solvate” describes a molecular complex comprising the drugsubstance and a stoichiometric or non-stoichiometric amount of one ormore solvent molecules (e.g., ethanol).

When the solvent is tightly bound to the drug the resulting complex willhave a well-defined stoichiometry that is independent of humidity. When,however, the solvent is weakly bound, as in channel solvates andhygroscopic compounds, the solvent content will be dependent on humidityand drying conditions. In such cases, the complex may benon-stoichiometric.

The term “hydrate” describes a solvate comprising the drug substance anda stoichiometric or non-stoichiometric amount of water.

The term “relative humidity” refers to the ratio of the amount of watervapor in air at a given temperature to the maximum amount of water vaporthat can be held at that temperature and pressure, expressed as apercentage.

The term “relative intensity” refers to an intensity value derived froma sample X-ray diffraction pattern. The complete ordinate range scalefor a diffraction pattern is assigned a value of 100. A peak havingintensity falling between about 50% to about 100% on this scaleintensity is termed very strong (vs); a peak having intensity fallingbetween about 50% to about 25% is termed strong (s). Additional weakerpeaks are present in typical diffraction patterns and are alsocharacteristic of a given polymorph, wherein the additional peaks aretermed medium (m), weak (w) and very weak (vw).

The term “slurry” refers to a solid substance suspended in a liquidmedium, typically water or an organic solvent.

The term “under vacuum” refers to typical pressures obtainable by alaboratory oil or oil-free diaphragm vacuum pump.

The term “treating”, as used herein, unless otherwise indicated, meansreversing, alleviating, or inhibiting the progress of the disorder orcondition to which such term applies, or one or more symptoms of suchdisorder or condition. The term “treatment”, as used herein, unlessotherwise indicated, refers to the act of “treating” as definedimmediately above. For example, the terms “treat”, “treating” and“treatment” can refer to a method of alleviating or abrogating aparticular disorder and/or one or more of its attendant symptoms.

The term “pharmaceutical composition” refers to a composition comprisingone or more of the salt or solid forms of tabernanthalog describedherein, and other chemical components, such asphysiologically/pharmaceutically acceptable carriers, diluents, vehiclesand/or excipients. The purpose of a pharmaceutical composition is tofacilitate administration of a compound to an organism, such as a humanor other mammals.

The term “pharmaceutically acceptable” “carrier”, “diluent”, “vehicle”,or “excipient” refers to a material (or materials) that may be includedwith a particular pharmaceutical agent to form a pharmaceuticalcomposition, and may be solid or liquid. Exemplary solid carriers arelactose, sucrose, talc, gelatin, agar, pectin, acacia, magnesiumstearate, stearic acid and the like. Exemplary liquid carriers aresyrup, peanut oil, olive oil, water and the like. Similarly, the carrieror diluent may include time-delay or time-release material known in theart, such as glyceryl monostearate or glyceryl distearate alone or witha wax, ethylcellulose, hydroxypropyl methylcellulose, methylmethacrylateand the like.

The term “compound of the present disclosure”, “compounds of the presentdisclosure”, “presently disclosed compound”, “presently disclosedcompounds”, “compound disclosed herein”, or “compounds disclosed herein”means the salt and solid form(s) of the tabernanthalog or the free basetabernanthalog.

II. Compounds

Recently, researchers reported some progress in developing compoundsthat maintain the potential therapeutic efficacy of the natural product,ibogaine, but lack ibogaine's toxicity and hallucinogenic effects. Forexample, the compound tabernanthalog (TBG), a simplified analog ofibogaine (or the iboga alkaloid tabernanthine),

was reported to be non-hallucinogenic, but have 5-HT2A activity.

(See, Dong et al. Cell, 184, 2779-2792; Olson et al. WO 2020/176599;Cameron, et al., Nature. 2021; 589(7842):474-479).

Olson et al. reported isolating tabernanthalog as a fumarate salt. Thepresent inventors observed that the properties of tabernanthalog and thedisclosed tabernanthalog fumarate could be improved upon to support itsuse in the clinical treatment of brain disorders. Accordingly, disclosedherein are novel forms of tabernanthalog, including salts and solidforms of tabernanthalog with improved properties. The disclosed formsare useful to treat various disorders, such as brain disorders. Alsodisclosed are methods for making salt and solid forms of tabernanthalogand method of administering the salt and solid forms of tabernanthalogto a subject in need thereof.

In some embodiments, the solid form of the compound (tabernanthalog) isa crystalline form of the tabernanthalog. In some embodiments, the solidform of tabernanthalog is a polymorph of tabernanthalog, such as apolymorph of the free base compound or a polymorph of a salt form. Insome embodiments, the solid form of the compound is a salt of thecompound. In some embodiments, the solid form of the compound is acrystalline salt form of the compound, such as an acid addition saltform. In one embodiment, the solid form of tabernanthalog is the freebase of tabernanthalog.

In one embodiment, a solid form of a tabernanthalog salt is made by amethod described in the Examples. The solid form of a tabernanthalogsalt made by the disclosed method may have at least one improvedproperty compared to another form of the tabernanthalog salt. In oneembodiment, the tabernanthalog salt solid form disclosed herein is acrystalline form that has an improved property relative to amorphoustabernanthalog salt. In one embodiment a crystalline form disclosedherein is a polymorph of tabernanthalog salt. In certain embodiments, adisclosed polymorph of tabernanthalog salt has an improved property overone or more other solid forms of tabernanthalog salt.

Also disclosed herein is a solid form of tabernanthalog fumarate that ismade by the method described in Example 1.

The solid form of tabernanthalog fumarate made by the disclosed methodmay have at least one improved property compared to another form oftabernanthalog fumarate. In one embodiment, the tabernanthalog fumaratesolid form disclosed herein is a crystalline form that has an improvedproperty relative to amorphous tabernanthalog fumarate. In oneembodiment a crystalline form disclosed herein is a polymorph oftabernanthalog fumarate. In certain embodiments, a disclosed polymorphof tabernanthalog fumarate has an improved property over one or moreother solid forms of tabernanthalog fumarate.

Salts

In some embodiments, tabernanthalog is prepared in the form of a salt oftabernanthalog. Suitable salts include pharmaceutically acceptable saltsof tabernanthalog. In some embodiments, the salt is provided as a solidform of tabernanthalog that is not, and does not comprise,tabernanthalog fumarate.

In some embodiments, the salt of tabernanthalog is formed from asuitable pharmaceutically acceptable acid, including, withoutlimitation, inorganic acids such as hydrobromic acid, sulfuric acid,nitric acid, phosphoric acid, and the like, as well as organic acidssuch as formic acid, acetic acid, trifluoroacetic acid, propionic acid,glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid,succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid,cinnamic acid, mandelic acid, benzene sulfonic acid, isethionic acid,methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid,salicylic acid, xinafoic acid and the like.

In other embodiments, the salt of tabernanthalog may be formed from asuitable pharmaceutically acceptable base, including, withoutlimitation, inorganic bases such as sodium, potassium, lithium,ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminumsalts and the like. Salts derived from pharmaceutically acceptableorganic bases include, but are not limited to, salts of primary,secondary, and tertiary amines, substituted amines including naturallyoccurring substituted amines, cyclic amines and basic ion exchangeresins, such as isopropylamine, trimethylamine, diethylamine,triethylamine, tripropylamine, tris(hydroxymethyl)aminomethane (Tris),ethanolamine, 2-dimethylaminoethanol, 2-diethylaminoethanol,dicyclohexylamine, lysine, arginine, histidine, caffeine, procaine,hydrabamine, choline, betaine, ethylenediamine, glucosamine,methylglucamine, theobromine, purines, piperazine, piperidine,N-ethylpiperidine, polyamine resins, and the like. Additionalinformation concerning pharmaceutically acceptable salts can be foundin, for example, S. M. Berge, et al., “Pharmaceutical Salts,” J. Pharm.Sci., 1977; 66:1-19 which is incorporated herein by reference.

In some embodiments, the salt is formed using an acid from Table 1.

TABLE 1 naphthalene-1,5-disulfonic acid citric acid sulfuric acidd-glucuronic acid ethane-1,2-disulfonic acid lactobionic acidp-toluenesulfonic acid D-glucoheptonic acid thiocyanic acid(−)-L-pyroglutamic acid methanesulfonic acid L-malic aciddodecylsulfuric acid hippuric acid naphthalene-2-sulfonic acidD-gluconic acid benzenesulfonic acid D,L-lactic acid oxalic acid oleicacid glycerophosphoric acid succinic acid ethanesulfonic acid, 2-hydroxyglutaric acid L-aspartic acid cinnamic acid maleic acid adipic acidphosphoric acid sebacic acid ethanesulfonic acid (+)-camphoric acidglutamic acid acetic acid pamoic (embonic) acid nicotinic acid glutaricacid, 2-oxo- isobutyric acid 2-naphthoic acid, 1-hydroxy propionic acidmalonic acid lauric acid gentisic acid stearic acid L-tartaric acidorotic acid fumaric acid carbonic acid galactaric (mucic) acid

The acid salts of tabernanthalog disclosed herein can have any suitablestoichiometric ratio of acid to tabernanthalog. In one embodiment, themolar ratio of acid is from about 0.4 to about 2.2 acid totabernanthalog, such as forms wherein the salt has a stoichiometricratio of from about 0.5 to about 2, such as about 0.5, about 1 or about2 moles of the acid for each mole of amine. In some embodiments, thetabernanthalog salt is a tabernanthalog sorbate salt, a tabernanthalogtartrate salt, a tabernanthalog maleate salt, or a tabernanthalogbenzoate salt.

In some embodiments, the tabernanthalog salt has at least one of thefollowing characteristics: (a) a unique powder diffraction pattern byXRPD, (b) a flat baseline leading to single melt event by DSC, (c) aflat baseline up to the melt by TGA, (d) a significantly reducedimpurity burden and absence of trace solvents by ¹H NMR, and (e) anoptically crystalline and reasonably equant morphology undercross-polarized filter.

In some embodiments, the tabernanthalog salt is tabernanthalog sorbatesalt. In specific embodiments, the tabernanthalog sorbate salt exhibitshigher crystallographic quality than the tabernanthalog fumarate salt.In other specific embodiments, the tabernanthalog sorbate salt providesgreater solvent and impurity rejection and give overall betterperformance in advanced physicochemical screening compared to othertabernanthalog salts. In yet other embodiments, the tabernanthalogsorbate salt is highly soluble in the SIF buffers with no observeddisproportionation.

In yet other embodiments, the tabernanthalog salt is at least about 95%pure as measured by HPLC.

In yet other embodiments, the tabernanthalog salt is at least about 96%pure as measured by HPLC.

In yet other embodiments, the tabernanthalog salt is at least about 97%pure as measured by HPLC.

In yet other embodiments, the tabernanthalog salt is at least about 98%pure as measured by HPLC.

In yet other embodiments, the tabernanthalog salt is at least about 99%pure as measured by HPLC.

In yet other embodiments, the tabernanthalog salt is at least about99.5% pure as measured by HPLC.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 95% pure as measured by HPLC.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 96% pure as measured by HPLC.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 97% pure as measured by HPLC.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 98% pure as measured by HPLC.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 99% pure as measured by HPLC.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 99.5% pure as measured by HPLC.

In yet other embodiments, the tabernanthalog salt is at least about 95%pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog salt is at least about 96%pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog salt is at least about 97%pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog salt is at least about 98%pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog salt is at least about 99%pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog salt is at least about99.5% pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 95% pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 96% pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 97% pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 98% pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 99% pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 99.5% pure as measured by UV chromatographic method.

In yet other embodiments, the tabernanthalog sorbate salt is at leastabout 99.64% pure as measured by UV chromatographic method.

Solid Forms

Embodiments of tabernanthalog of the present disclosure are in a solidform. The solid form may be a crystalline form or an amorphous form. Insome embodiments, the solid form is a crystalline form. In someembodiments, the solid form of tabernanthalog is a salt. And in certainembodiments, the solid form is a crystalline salt form of the compound.A person of ordinary skill in the art understands that solid forms oftabernanthalog, such as crystalline forms including salt and non-saltcrystalline forms of tabernanthalog, may exist in more than one crystalform. Such different forms are referred to as polymorphs. In someembodiments, the disclosed compounds are particular polymorphs oftabernanthalog or tabernanthalog salts.

In some embodiments, the solid form of tabernanthalog disclosed hereinis selected to be a crystalline form, such as a particular polymorph ofa crystalline form of tabernanthalog, that provides one or more desiredproperties. In one embodiment, the crystalline form offers advantagesover the amorphous form of the molecule. In another embodiment, thedisclosed polymorph offers improved properties as compared to anotherpolymorph of tabernanthalog. The tabernanthalog may be a salt or freebase compound. The one or more desired properties may include, but arenot limited to, physical properties, including but not limited to,hygroscopic properties, solubility in water and/or organic solvents,melting point, glass transition temperature, flowability, and/orstability, such as thermal stability, mechanical stability, shelf life,stability against polymorphic transition, etc.; chemical properties,such as, but not limited to, reactivity, compatibility with excipientsand/or delivery vehicles; and/or pharmacokinetic properties, such as,but not limited to, bioavailability, absorption, distribution,metabolism, excretion, toxicity including cytotoxicity, dissolutionrate, and/or half-life.

The desired polymorph may be produced by techniques known to persons ofordinary skill in the art. Such techniques include, but are not limitedto, crystallization in particular solvents and/or at particulartemperatures, supersaturation, using a precipitation agent, such as asalt, glycol, alcohol, etc., co-crystallization, lyophilization, spraydrying, freeze drying, and/or complexing with an inert agent.

Techniques to identify a particular solid form of tabernanthalog areknown to persons of ordinary skill in the art, and include, but are notlimited to, X-ray crystallography, X-ray diffraction, electroncrystallography, powder diffraction, including X-ray, neutron, orelectron diffraction, X-ray fiber diffraction, small-angle X-rayscattering, and/or melting point.

It will be understood that characterization data present in the Examplesis considered to be part of the present invention. In some embodiments,each of the XRPD tables located in the Examples which contain XRPDsignals/peaks are considered as inventive entities individually andseparately from the methods of producing the particular XPRDcharacterization. These tables are referred to by embodiments in thedetailed description and are considered part of the detaileddescription.

Tabernanthalog Fumarate Salt

In some embodiments, the tabernanthalog fumarate salt is crystallinepolymorphic unary fumarate salt of Tabernanthalog.

In some embodiments, the tabernanthalog fumarate salt is crystallinepolymorphic hemi-fumarate salt of Tabernanthalog.

In some embodiments, the tabernanthalog fumarate salt is crystallinepolymorphic salt of Tabernanthalog of Form A, Form B, Form I, or amixture thereof.

In some embodiments, the tabernanthalog fumarate salt is crystallinepolymorphic salt of tabernanthalog with Pattern #1, Pattern #2a, Pattern#2b, Pattern #2c, Pattern #2d, Pattern #3, Pattern #4a, Pattern #4b,Pattern #5, Pattern #6a, Pattern #6b, Pattern #7, Pattern #8, Pattern#9, Pattern #10, Pattern #11, Pattern #12, Pattern #13, Pattern #14,Pattern #15, Pattern #16, Pattern #17, Pattern #18, Pattern #19, Pattern#20, Pattern #21, Pattern #22, or a mixture thereof.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #12) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 16.3°2θ, 20.2°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumarate(Pattern #12) characterized by XRPD signals at 16.3°2θ, 20.2°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #12) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 20.2°2θ, 21.4°2θ, and 18.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate (Pattern #12) characterized by XRPD signals at 25.5°2θ,16.3°2θ, 20.2°2θ, 21.4°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #12) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 20.2°2θ, 21.4°2θ, 18.1°2θ, 26.8°2θ, and8.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #12) characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 20.2°2θ, 21.4°2θ, 18.1°2θ, 26.8°2θ,and 8.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #12) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 20.2°2θ, 21.4°2θ, 18.1°2θ, 26.8°2θ,8.2°2θ, 22.9°2θ, 9.0°2θ, and 16.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate (Pattern #12)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 20.2°2θ, 21.4°2θ,18.1°2θ, 26.8°2θ, 8.2°2θ, 22.9°2θ, 9.0°2θ, and 16.6°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #12) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, or eighteen XRPD signals selected from those setforth in Table 6.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #2a) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumarate(Pattern #2a) characterized by XRPD signals at 25.6°2θ, 16.3°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #2a) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 17.1°2θ, 9.1°2θ, and 27.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate (Pattern #2a) characterized by XRPD signals at 25.6°2θ,16.3°2θ, 17.1°2θ, 9.1°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #2a) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 17.1°2θ, 9.1°2θ, 27.3°2θ, 18.1°2θ, and22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #2a) characterized byXRPD signals at 25.6°2θ, 16.3°2θ, 17.1°2θ, 9.1°2θ, 27.3°2θ, 18.1°2θ, and22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #2a) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 17.1°2θ, 9.1°2θ, 27.3°2θ, 18.1°2θ,22.9°2θ, 26.8°2θ, 15.6°2θ, and 12.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 17.1°2θ, 9.1°2θ,27.3°2θ, 18.1°2θ, 22.9°2θ, 26.8°2θ, 15.6°2θ, and 12.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2a) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, or eighteen XRPD signals selected from those setforth in Table 7.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #15) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 16.3°2θ, 16.9°2θ, and 24.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumarate(Pattern #15) characterized by XRPD signals at 16.3°2θ, 16.9°2θ, and24.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #15) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 16.3°2θ, 16.9°2θ, 24.5°2θ, 25.6°2θ, and 23.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate (Pattern #15) characterized by XRPD signals at 16.3°2θ,16.9°2θ, 24.5°2θ, 25.6°2θ, and 23.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #15) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 16.3°2θ, 16.9°2θ, 24.5°2θ, 25.6°2θ, 23.4°2θ, 8.5°2θ, and17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #15) characterized byXRPD signals at 16.3°2θ, 16.9°2θ, 24.5°2θ, 25.6°2θ, 23.4°2θ, 8.5°2θ, and17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #15) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 16.3°2θ, 16.9°2θ, 24.5°2θ, 25.6°2θ, 23.4°2θ, 8.5°2θ,17.0°2θ, 17.7°2θ, 19.3°2θ, and 9.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate (Pattern #15)characterized by XRPD signals at 16.3°2θ, 16.9°2θ, 24.5°2θ, 25.6°2θ,23.4°2θ, 8.5°2θ, 17.0°2θ, 17.7°2θ, 19.3°2θ, and 9.5°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #15) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, or twenty-five XRPD signals selected fromthose set forth in Table 8.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumarate(Pattern #1) characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and 9.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate (Pattern #1) characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 9.0°2θ, 26.8°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 9.0°2θ, 26.8°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 9.0°2θ, 26.8°2θ,18.1°2θ, 17.7°2θ, 27.2°2θ, and 21.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,9.0°2θ, 26.8°2θ, 18.1°2θ, 17.7°2θ, 27.2°2θ, and 21.1°2θ(±0.2°2θ;±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, or eighteen XRPD signals selected from those setforth in Table 9.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumarate(Pattern #1) characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and 26.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate (Pattern #1) characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 26.1°2θ, 18.1°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 26.1°2θ, 18.1°2θ,and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 26.1°2θ, 18.1°2θ,21.8°2θ, 9.1°2θ, 21.3°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 26.1°2θ, 18.1°2θ,21.8°2θ, 9.1°2θ, 21.3°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, or seventeen XRPD signals selected from those set forth inTable 10.

In some embodiments, the solid form of tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate (Pattern #5) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 8.3°2θ, 17.0°2θ, and 11.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation). In some embodiments, the solid form of tabernanthaloghemifumarate is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.3°2θ, 17.0°2θ, and 11.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate (Pattern #5) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 8.3°2θ, 17.0°2θ, 11.1°2θ, 15.4°2θ, and 21.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate is crystalline tabernanthaloghemifumarate (Pattern #5) characterized by XRPD signals at 8.3°2θ,17.0°2θ, 11.1°2θ, 15.4°2θ, and 21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate(Pattern #5) is characterized by one, two, three, four, five, or sixXRPD signals selected from those set forth in Table 11.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 15.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #9) is crystallinetabernanthalog monofumarate (Pattern #9) characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, and 15.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 15.9°2θ, 24.6°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #9)is crystalline tabernanthalog monofumarate (Pattern #9) characterized byXRPD signals at 25.6°2θ, 16.4°2θ, 15.9°2θ, 24.6°2θ, and 25.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 15.9°2θ, 24.6°2θ,25.3°2θ, 19.4°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #9) is crystalline tabernanthalog monofumarate(Pattern #9) characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 15.9°2θ,24.6°2θ, 25.3°2θ, 19.4°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 15.9°2θ, 24.6°2θ,25.3°2θ, 19.4°2θ, 9.1°2θ, 18.1°2θ, 26.9°2θ, and 7.9°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #9) is crystalline tabernanthalogmonofumarate (Pattern #9) characterized by XRPD signals at 25.6°2θ,16.4°2θ, 15.9°2θ, 24.6°2θ, 25.3°2θ, 19.4°2θ, 9.1°2θ, 18.1°2θ, 26.9°2θ,and 7.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #9) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPDsignals selected from those set forth in Table 12.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.9°2θ, 25.6°2θ, and 16.4°2θ(+0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #10) is crystallinetabernanthalog monofumarate (Pattern #10) characterized by XRPD signalsat 16.9°2θ, 25.6°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.9°2θ, 25.6°2θ, 16.4°2θ, 21.4°2θ, and23.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #10)is crystalline tabernanthalog monofumarate (Pattern #10) characterizedby XRPD signals at 16.9°2θ, 25.6°2θ, 16.4°2θ, 21.4°2θ, and23.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.9°2θ, 25.6°2θ, 16.4°2θ, 21.4°2θ,23.5°2θ, 8.2°2θ, and 15.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #10) is crystalline tabernanthalog monofumarate(Pattern #10) characterized by XRPD signals at 16.9°2θ, 25.6°2θ,16.4°2θ, 21.4°2θ, 23.5°2θ, 8.2°2θ, and 15.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.9°2θ, 25.6°2θ, 16.4°2θ, 21.4°2θ,23.5°2θ, 8.2°2θ, 15.2°2θ, 19.8°2θ, 9.1°2θ, and 10.8°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #10) is crystalline tabernanthalogmonofumarate (Pattern #10) characterized by XRPD signals at 16.9°2θ,25.6°2θ, 16.4°2θ, 21.4°2θ, 23.5°2θ, 8.2°2θ, 15.2°2θ, 19.8°2θ, 9.1°2θ,and 10.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #10) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPDsignals selected from those set forth in Table 13.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 25.5°2θ, and 15.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #8) is crystallinetabernanthalog monofumarate (Pattern #8) characterized by XRPD signalsat 16.3°2θ, 25.5°2θ, and 15.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 25.5°2θ, 15.8°2θ, 24.3°2θ, and7.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #8)is crystalline tabernanthalog monofumarate (Pattern #8) characterized byXRPD signals at 16.3°2θ, 25.5°2θ, 15.8°2θ, 24.3°2θ, and 7.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 25.5°2θ, 15.8°2θ, 24.3°2θ, 7.6°2θ,19.1°2θ, and 20.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate (Pattern#8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 16.3°2θ, 25.5°2θ, 15.8°2θ, 24.3°2θ,7.6°2θ, 19.1°2θ, and 20.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 25.5°2θ, 15.8°2θ, 24.3°2θ, 7.6°2θ,19.1°2θ, and 20.6°2θ, 18.1°2θ, 9.0°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #8) is crystalline tabernanthalogmonofumarate (Pattern #8) characterized by XRPD signals at 16.3°2θ,25.5°2θ, 15.8°2θ, 24.3°2θ, 7.6°2θ, 19.1°2θ, and 20.6°2θ, 18.1°2θ,9.0°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #8) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, ortwenty-two XRPD signals selected from those set forth in Table 14.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, and 8.2°2θ(±0.2°2θ;+0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #6b) is crystallinetabernanthalog monofumarate (Pattern #6b) characterized by XRPD signalsat 19.5°2θ, 26.1°2θ, and 8.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, 8.2°2θ, 13.0°2θ, and16.5°2θ (+0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #6b)is crystalline tabernanthalog monofumarate (Pattern #6b) characterizedby XRPD signals at 19.5°2θ, 26.1°2θ, 8.2°2θ, 13.0°2θ, and 16.5°2θ(+0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, 8.2°2θ, 13.0°2θ, 16.5°2θ,19.6°2θ, and 20.6°2θ (+0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 26.1°2θ, 8.2°2θ, 13.0°2θ,16.5°2θ, 19.6°2θ, and 20.6°2θ (+0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.3°2θ, 19.5°2θ, 26.1°2θ, 8.2°2θ, 13.0°2θ, 16.5°2θ, 19.6°2θ, and 20.6°2θ (+0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #6b) is crystalline tabernanthalog monofumarate(Pattern #6b) characterized by XRPD signals at 25.3°2θ, 19.5°2θ,26.1°2θ, 8.2°2θ, 13.0°2θ, 16.5°2θ, 19.6°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6b) is characterized by one, two, three, four, five, six,seven, or eight XRPD signals selected from those set forth in Table 15.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, and 16.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #2c) is crystallinetabernanthalog monofumarate (Pattern #2c) characterized by XRPD signalsat 25.7°2θ, 16.4°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, 16.1°2θ, 9.2°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #2c)is crystalline tabernanthalog monofumarate (Pattern #2c) characterizedby XRPD signals at 25.7°2θ, 16.4°2θ, 16.1°2θ, 9.2°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, 16.1°2θ, 9.2°2θ, 18.2°2θ,7.9°2θ, and 24.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate (Pattern#2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 25.7°2θ, 16.4°2θ, 16.1°2θ, 9.2°2θ,18.2°2θ, 7.9°2θ, and 24.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, 16.1°2θ, 9.2°2θ, 18.2°2θ,7.9°2θ, 24.8°2θ, 26.9°2θ, 19.5°2θ, and 7.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #2c) is crystalline tabernanthalogmonofumarate (Pattern #2c) characterized by XRPD signals at 25.7°2θ,16.4°2θ, 16.1°2θ, 9.2°2θ, 18.2°2θ, 7.9°2θ, 24.8°2θ, 26.9°2θ, 19.5°2θ,and 7.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPDsignals selected from those set forth in Table 16.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, and 16.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #7) is crystallinetabernanthalog monofumarate (Pattern #7) characterized by XRPD signalsat 25.7°2θ, 16.4°2θ, and 16.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, 16.0°2θ, 19.5°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #7)is crystalline tabernanthalog monofumarate (Pattern #7) characterized byXRPD signals at 25.7°2θ, 16.4°2θ, 16.0°2θ, 19.5°2θ, and 21.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, 16.0°2θ, 19.5°2θ,21.4°2θ, 7.3°2θ, and 25.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #7) is crystalline tabernanthalog monofumarate(Pattern #7) characterized by XRPD signals at 25.7°2θ, 16.4°2θ, 16.0°2θ,19.5°2θ, 21.4°2θ, 7.3°2θ, and 25.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, 16.0°2θ, 19.5°2θ,21.4°2θ, 7.3°2θ, 25.0°2θ, 9.2°2θ, 18.2°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #7) is crystalline tabernanthalogmonofumarate (Pattern #7) characterized by XRPD signals at 25.7°2θ,16.4°2θ, 16.0°2θ, 19.5°2θ, 21.4°2θ, 7.3°2θ, 25.0°2θ, 9.2°2θ, 18.2°2θ,and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #7) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, or twenty XRPD signals selectedfrom those set forth in Table 17. In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #11) is crystalline tabernanthalogmonofumarate (Pattern #11) characterized by two or more, or three ormore XRPD signals selected from the group consisting of 25.6°2θ,16.0°2θ, and 21.5°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by XRPD signals at 25.6°2θ, 16.0°2θ, and 21.5°2θ (±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 21.5°2θ, 20.2°2θ, and16.3°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #11)is crystalline tabernanthalog monofumarate (Pattern #11) characterizedby XRPD signals at 25.6°2θ, 16.0°2θ, 21.5°2θ, 20.2°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 21.5°2θ, 20.2°2θ, and16.3°2θ, 7.4°2θ, and 17.2°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #11) is crystalline tabernanthalog monofumarate(Pattern #11) characterized by XRPD signals at 25.6°2θ, 16.0°2θ,21.5°2θ, 20.2°2θ, and 16.3°2θ, 7.4°2θ, and 17.2°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 21.5°2θ, 20.2°2θ, and16.3°2θ, 7.4°2θ, 17.2°2θ, 20.7°2θ, 23.7°2θ, and 26.8°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #11) is crystallinetabernanthalog monofumarate (Pattern #11) characterized by XRPD signalsat 25.6°2θ, 16.0°2θ, 21.5°2θ, 20.2°2θ, and 16.3°2θ, 7.4°2θ, 17.2°2θ,20.7°2θ, 23.7°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #11) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, or nineteen XRPD signals selected fromthose set forth in Table 18.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, and 16.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 25.7°2θ, 16.5°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 16.8°2θ, 22.4°2θ, and9.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #1)is crystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 25.7°2θ, 16.5°2θ, 16.8°2θ, 22.4°2θ, and 9.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 16.8°2θ, 22.4°2θ, 9.2°2θ,26.9°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate (Pattern#1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.7°2θ, 16.5°2θ, 16.8°2θ, 22.4°2θ,9.2°2θ, 26.9°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 16.8°2θ, 22.4°2θ, 9.2°2θ,26.9°2θ, 19.4°2θ, 18.2°2θ, 26.2°2θ, and 20.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #1) is crystalline tabernanthalogmonofumarate (Pattern #1) characterized by XRPD signals at 25.7°2θ,16.5°2θ, 16.8°2θ, 22.4°2θ, 9.2°2θ, 26.9°2θ, 19.4°2θ, 18.2°2θ, 26.2°2θ,and 20.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, or seventeen XRPD signals selected from those set forth inTable 19.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 9.1°2θ, and 16.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #2c) is crystallinetabernanthalog monofumarate (Pattern #2c) characterized by XRPD signalsat 25.5°2θ, 9.1°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 9.1°2θ, 16.3°2θ, 25.1°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #2c)is crystalline tabernanthalog monofumarate (Pattern #2c) characterizedby XRPD signals at 25.5°2θ, 9.1°2θ, 16.3°2θ, 25.1°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 9.1°2θ, 16.3°2θ, 25.1°2θ, 18.0°2θ, 21.9°2θ, and 14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #2c) is crystalline tabernanthalog monofumarate(Pattern #2c) characterized by XRPD signals at 25.5°2θ, 9.1°2θ, 16.3°2θ,25.1°2θ, 18.0°2θ, 21.9°2θ, and 14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 9.1°2θ, 16.3°2θ, 25.1°2θ, 18.0°2θ, 21.9°2θ, 14.2°2θ, 17.4°2θ, 26.7°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate (Pattern #2c) is crystalline tabernanthalogmonofumarate (Pattern #2c) characterized by XRPD signals at 25.5°2θ,9.1°2θ, 16.3°2θ, 25.1°2θ, 18.0°2θ, 21.9°2θ, 14.2°2θ, 17.4°2θ, 26.7°2θ,and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, or twelve XRPD signals selected fromthose set forth in Table 20.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, and 19.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 25.7°2θ, 16.5°2θ, and 19.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 19.5°2θ, 16.8°2θ, and18.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #1)is crystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 25.7°2θ, 16.5°2θ, 19.5°2θ, 16.8°2θ, and 18.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 19.5°2θ, 16.8°2θ,18.3°2θ, 22.4°2θ, and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #1) is crystalline tabernanthalog monofumarate(Pattern #1) characterized by XRPD signals at 25.7°2θ, 16.5°2θ, 19.5°2θ,16.8°2θ, 18.3°2θ, 22.4°2θ, and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 19.5°2θ, 16.8°2θ,18.3°2θ, 22.4°2θ, 27.4°2θ, 9.2°2θ, 27.0°2θ, and 26.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 25.7°2θ, 16.5°2θ, 19.5°2θ, 16.8°2θ, 18.3°2θ, 22.4°2θ, 27.4°2θ,9.2°2θ, 27.0°2θ, and 26.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, or nineteen XRPD signals selected fromthose set forth in Table 21.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 25.7°2θ, 16.5°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 19.4°2θ, 16.8°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #1)is crystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 25.7°2θ, 16.5°2θ, 19.4°2θ, 16.8°2θ, and 18.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 19.4°2θ, 16.8°2θ,18.2°2θ, 27.0°2θ, and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #1) is crystalline tabernanthalog monofumarate(Pattern #1) characterized by XRPD signals at 25.7°2θ, 16.5°2θ, 19.4°2θ,16.8°2θ, 18.2°2θ, 27.0°2θ, and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.5°2θ, 19.4°2θ, 16.8°2θ,18.2°2θ, 27.0°2θ, 27.4°2θ, 22.4°2θ, 9.2°2θ, and 26.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 25.7°2θ, 16.5°2θ, 19.4°2θ, 16.8°2θ, 18.2°2θ, 27.0°2θ, 27.4°2θ,22.4°2θ, 9.2°2θ, and 26.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, or seventeen XRPD signals selected from those set forth inTable 22.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.7°2θ, and 22.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 16.4°2θ, 25.7°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.7°2θ, 22.4°2θ, 16.9°2θ, and19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #1)is crystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 16.4°2θ, 25.7°2θ, 22.4°2θ, 16.9°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.7°2θ, 22.4°2θ, 16.9°2θ,19.4°2θ, 18.2°2θ, and 27.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #1) is crystalline tabernanthalog monofumarate(Pattern #1) characterized by XRPD signals at 16.4°2θ, 25.7°2θ, 22.4°2θ,16.9°2θ, 19.4°2θ, 18.2°2θ, and 27.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation. In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #1) is crystalline tabernanthalog monofumarate(Pattern #1) characterized by two or more, or three or more XRPD signalsselected from the group consisting of 16.4°2θ, 25.7°2θ, 22.4°2θ,16.9°2θ, 19.4°2θ, 18.2°2θ, 27.0°2θ, 20.4°2θ, 25.4°2θ, and9.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate (Pattern #1)is crystalline tabernanthalog monofumarate (Pattern #1) characterized byXRPD signals at 16.4°2θ, 25.7°2θ, 22.4°2θ, 16.9°2θ, 19.4°2θ, 18.2°2θ,27.0°2θ, 20.4°2θ, 25.4°2θ, and 9.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, or seventeen XRPD signals selected from those set forth inTable 23.

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogfumarate salt is crystalline tabernanthalog fumarate salt characterizedby XRPD signals at 25.6°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog fumarate salt is crystalline tabernanthalog fumarate saltcharacterized by XRPD signals at 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, 22.3°2θ, 27.3°2θ,26.8°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, 22.3°2θ,27.3°2θ, 26.8°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog fumarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, oreighteen XRPD signals selected from those set forth in Table 24.

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogfumarate salt is crystalline tabernanthalog fumarate salt characterizedby XRPD signals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting25.5°2θ, 16.3°2θ, 19.3°2θ, 16.6°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog fumarate salt is crystalline tabernanthalog fumarate saltcharacterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.6°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting25.5°2θ, 16.3°2θ, 19.3°2θ, 16.6°2θ, 22.3°2θ, 27.2°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.6°2θ, 22.3°2θ, 27.2°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.5°2θ, 16.3°2θ, 19.3°2θ, 16.6°2θ, 22.3°2θ, 27.2°2θ, and 18.1°2θ,26.8°2θ, 25.1°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogfumarate salt is crystalline tabernanthalog fumarate salt characterizedby XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.6°2θ, 22.3°2θ, 27.2°2θ,and 18.1°2θ, 26.8°2θ, 25.1°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog fumarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, or twenty XRPD signals selected from those set forthin Table 25.

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogfumarate salt is crystalline tabernanthalog fumarate salt characterizedby XRPD signals at 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog fumarate salt is crystalline tabernanthalog fumarate saltcharacterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ, 22.4°2θ, 27.3°2θ,26.9°2θ, and 25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ, 22.4°2θ,27.3°2θ, 26.9°2θ, and 25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog fumarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, or twenty-two XRPD signalsselected from those set forth in Table 26.

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogfumarate salt is crystalline tabernanthalog fumarate salt characterizedby XRPD signals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog fumarate salt is crystalline tabernanthalog fumarate saltcharacterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 27.2°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 27.2°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 27.2°2θ, 9.1°2θ, 18.1°2θ,26.8°2θ, and 25.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 27.2°2θ, 9.1°2θ,18.1°2θ, 26.8°2θ, and 25.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog fumarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, or nineteen XRPD signals selected from those set forth inTable 27.

In some embodiments, the solid form of tabernanthalog monofumarate saltis crystalline tabernanthalog monofumarate salt (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, and 18.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt is crystalline tabernanthalogmonofumarate salt (Pattern #1) characterized by XRPD signals at 25.6°2θ,16.0°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltis crystalline tabernanthalog monofumarate salt (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt iscrystalline tabernanthalog monofumarate salt (Pattern #1) characterizedby XRPD signals at 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltis crystalline tabernanthalog monofumarate salt (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ,21.4°2θ, 26.8°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt is crystalline tabernanthalog monofumarate salt(Pattern #1) characterized by XRPD signals at 25.6°2θ, 16.0°2θ, 18.0°2θ,16.3°2θ, 21.4°2θ, 26.8°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltis crystalline tabernanthalog monofumarate salt (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ,21.4°2θ, 26.8°2θ, 23.0°2θ, 25.9°2θ, 15.5°2θ, and 11.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt is crystalline tabernanthalogmonofumarate salt (Pattern #1) characterized by XRPD signals at 25.6°2θ,16.0 °2θ, 18.0°2θ, 16.3°2θ, 21.4°2θ, 26.8°2θ, 23.0°2θ, 25.9°2θ, 15.5°2θ,and 11.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate salt(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPDsignals selected from those set forth in Table 29.

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogfumarate is crystalline tabernanthalog fumarate characterized by XRPDsignals 25.6°2θ, 16.4°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog fumarate is crystalline tabernanthalog fumaratecharacterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, 9.1°2θ, 18.1°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog fumarate is crystallinetabernanthalog fumarate characterized by XRPD signals at 25.6°2θ,16.4°2θ, 19.3°2θ, 16.7°2θ, 9.1°2θ, 18.1°2θ, and 22.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, 9.1°2θ, 18.1°2θ, 22.4°2θ, 27.3°2θ,26.8°2θ, and 25.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by XRPD signals at25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, 9.1°2θ, 18.1°2θ, 22.4°2θ, 27.3°2θ,26.8°2θ, and 25.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog fumarate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, or twenty-two XRPD signalsselected from those set forth in Table 30.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5° 20, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #6a characterized by XRPD signals at 19.5°2θ, 16.5°20, and 20.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #6a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, and 26.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #6a) is crystallinetabernanthalog monofumarate pattern #6a characterized by XRPD signals at19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ,26.1°2θ, 22.0°2θ, and 33.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #6a) is crystalline tabernanthalog monofumaratepattern #6a characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ,25.3°2θ, 26.1°2θ, 22.0°2θ, and 33.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ,26.1°2θ, 22.0°2θ, 33.5°2θ, 12.9°2θ, and 37.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ,26.1°2θ, 22.0°2θ, 33.5°2θ, 12.9°2θ, and 37.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#6a is characterized by one, two, three, four, five, six, seven, eight,or nine XRPD signals selected from those set forth in Table 31.

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.0°2θ, 11.3°2θ, and 20.2 (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of Tabernanthalog·0.5Fumarate is crystalline Tabernanthalog·0.5 Fumarate characterized byXRPD signals at 17.0°2θ, 11.3°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.0°2θ, 11.3°2θ, 20.2°2θ, 23.6°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·0.5 Fumarate is crystalline Tabernanthalog·0.5 Fumaratecharacterized by XRPD signals at 17.0°2θ, 11.3°2θ, 20.2°2θ, 23.6°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.0°2θ, 11.3°2θ, 20.2°2θ, 23.6°2θ, 21.4°2θ, 15.5°2θ, and22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by XRPD signals at17.0°2θ, 11.3°2θ, 20.2°2θ, 23.6°2θ, 21.4°2θ, 15.5°2θ, and22.6°2θ(±0.2°2θ; ±0.1 θ2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.0°2θ, 11.3°2θ, 20.2°2θ, 23.6°2θ, 21.4°2θ, 15.5°2θ, 22.6°2θ, 8.2°2θ,24.2°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by XRPD signals at17.0°2θ, 11.3°2θ, 20.2°2θ, 23.6°2θ, 21.4°2θ, 15.5°2θ, 22.6°2θ, 8.2°2θ,24.2°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog·0.5 Fumarate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, or twenty-one XRPD signals selected fromthose set forth in Table 32.

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate Pattern #14 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 8.2°2θ, 15.5°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·0.5 Fumarate is crystalline Tabernanthalog·0.5 FumaratePattern #14 characterized by XRPD signals at 8.2°2θ, 15.5°2θ, and17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate Pattern #14 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, and 20.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of Tabernanthalog·0.5 Fumarate is crystalline Tabernanthalog·0.5Fumarate Pattern #14 characterized by XRPD signals at 8.2°2θ, 15.5°2θ,17.0°2θ, 22.6°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate Pattern #14 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, and23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate Pattern #14 characterized byXRPD signals at 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, and23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate Pattern #14 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ,23.7°2θ, 24.8°2θ, 21.5°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate Pattern #14 characterized byXRPD signals at 8.2°2θ, 15.5°2θ, 17.0 °2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ,23.7°2θ, 24.8°2θ, 21.5°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline Tabernanthalog·0.5 Fumarate Pattern#14 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPDsignals selected from those set forth in Table 32A.

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #14) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 11.3°2θ, 8.2°2θ, and 17.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #14) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 11.3°2θ, 8.2°2θ, and 17.1°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #14) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 11.3°2θ, 8.2°2θ, 17.1°2θ, 21.5°2θ, and23.7°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #14) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 11.3°2θ, 8.2°2θ, 17.1°2θ, 21.5°2θ,23.7°2θ, 22.7°2θ, and 20.3°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthaloghemifumarate (Pattern #14) is crystalline tabernanthalog hemifumarate(Pattern #5) characterized by XRPD signals at 11.3°2θ, 8.2°2θ, 17.1°2θ,21.5°2θ, 23.7°2θ, 22.7°2θ, 20.3°2θ, 25.5°2θ, 15.6°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate(Pattern #14) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, or fifteenXRPD signals selected from those set forth in Table 123.

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 4.3°2θ,17.5°2θ, and 19.3°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by XRPD signals at4.3°2θ, 17.5°2θ, and 19.3°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 4.3°2θ,17.5°2θ, 19.3°2θ, 20.1°2θ, and 14.5°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogfumarate is crystalline tabernanthalog fumarate characterized by XRPDsignals 4.3°2θ, 17.5°2θ, 19.3°2θ, 20.1°2θ, and 14.5°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 4.3°2θ,17.5°2θ, 19.3°2θ, 20.1°2θ, 14.5°2θ, 21.0°2θ, and 23.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog fumarate is crystalline tabernanthalog fumaratecharacterized by XRPD signals at 4.3°2θ, 17.5°2θ, 19.3°2θ, 20.1°2θ,14.5°2θ, 21.0°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog fumarate iscrystalline tabernanthalog fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 4.3°2θ,17.5°2θ, 19.3°2θ, 20.1°2θ, 14.5°2θ, 21.0°2θ, 23.7°2θ, 18.7°2θ, 23.3°2θ,and 31.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog fumarate is crystallinetabernanthalog fumarate characterized by XRPD signals at 4.3°2θ,17.5°2θ, 19.3°2θ, 20.1°2θ, 14.5°2θ, 21.0°2θ, 23.7°2θ, 18.7°2θ, 23.3°2θ,and 31.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog fumarate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three,twenty-four, twenty-five, twenty-six, twenty-seven, or twenty-eight XRPDsignals selected from those set forth in Table 33.

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of16.9°2θ, 25.4°2θ, and 22.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of Tabernanthalog·0.5Fumarate is crystalline Tabernanthalog·0.5 Fumarate characterized byXRPD signals at 16.9°2θ, 25.4°2θ, and 22.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of16.9°2θ, 25.4°2θ, 22.7°2θ, 27.2°2θ, and 20.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·0.5 Fumarate is crystalline Tabernanthalog·0.5 Fumaratecharacterized by XRPD signals 16.9°2θ, 25.4°2θ, 22.7°2θ, 27.2°2θ, and20.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of16.9°2θ, 25.4°2θ, 22.7°2θ, 27.2°2θ, 20.5°2θ, 16.2°2θ, and15.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of E Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by XRPD signals16.9°2θ, 25.4°2θ, 22.7°2θ, 27.2°2θ, 20.5°2θ, 16.2°2θ, and15.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of16.9°2θ, 25.4°2θ, 22.7°2θ, 27.2°2θ, 20.5°2θ, 16.2°2θ, 15.5°2θ, 24.7°2θ,20.8°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of Tabernanthalog·0.5 Fumarate iscrystalline Tabernanthalog·0.5 Fumarate characterized by XRPD signals at16.9°2θ, 25.4°2θ, 22.7°2θ, 27.2°2θ, 20.5°2θ, 16.2°2θ, 15.5°2θ, 24.7°2θ,20.8°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog·0.5 Fumarate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeenXRPD signals selected from those set forth in Table 34.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #2b characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 18.0°2θ, 9.0°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #2b characterized by XRPD signals 25.5°2θ, 16.3°2θ,18.0°2θ, 9.0°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 18.0°2θ, 9.0°2θ, 26.8°2θ, 22.5°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized byXRPD signals 25.5°2θ, 16.3°2θ, 18.0°2θ, 9.0°2θ, 26.8°2θ, 22.5°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 18.0°2θ, 9.0°2θ, 26.8°2θ, 22.5°2θ,22.3°2θ, 25.0°2θ, 17.4°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 18.0°2θ, 9.0°2θ, 26.8°2θ, 22.5°2θ,22.3°2θ, 25.0°2θ, 17.4°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#2b is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, or thirteen XRPD signals selected from thoseset forth in Table 37.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #1 characterized by XRPD signals at 25.6°2θ, 16.4°2θ, and19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, and 9.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #1 characterized by XRPD signals 25.6°2θ, 16.4°2θ,19.4°2θ, 16.8°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ,22.4°2θ, 27.3°2θ, 25.3°2θ, and 6.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 9.1°2θ, 18.2°2θ, 22.4°2θ,27.3°2θ, 25.3°2θ, and 6.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#1 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, or twenty XRPD signals selected fromthose set forth in Table 38.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #1 characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and 18.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #1 characterized by XRPD signals 25.5°2θ, 16.3°2θ,19.3°2θ, 16.7°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 22.3°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 22.3°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 22.3°2θ,27.2°2θ, 9.1°2θ, 17.8°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 22.3°2θ,27.2°2θ, 9.1°2θ, 17.8°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#1 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, or eighteen XRPD signals selected from those set forth inTable 39.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.7°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #1 characterized by XRPD signals at 25.7°2θ, 16.4°2θ, and19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.7°2θ, 16.4°2θ, 19.4°2θ, 16.9°2θ, and 18.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #1 characterized by XRPD signals 25.7°2θ, 16.4°2θ,19.4°2θ, 16.9°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.7°2θ, 16.4°2θ, 19.4°2θ, 16.9°2θ, 18.2°2θ, 22.5°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1characterized by XRPDsignals of 25.7°2θ, 16.4°2θ, 19.4°2θ, 16.9°2θ, 18.2°2θ, 22.5°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.7°2θ, 16.4°2θ, 19.4°2θ, 16.9°2θ, 18.2°2θ, 22.5°2θ,27.3°2θ, 27.0°2θ, 9.2°2θ, and 17.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals at 25.7°2θ, 16.4°2θ, 19.4°2θ, 16.9°2θ, 18.2°2θ, 22.5°2θ,27.3°2θ, 27.0°2θ, 9.2°2θ, and 17.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#1 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, or eighteen XRPD signals selected from those set forth inTable 40.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate pattern #1 is crystalline tabernanthalogmonofumarate pattern #1 characterized by XRPD signals at 25.6°2θ,16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.8°2θ, and 25.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #1 characterized by XRPD signals 25.6°2θ, 16.3°2θ,19.3°2θ, 16.8°2θ, and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.8°2θ, 25.4°2θ, 18.2°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals of 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.8°2θ, 25.4°2θ, 18.2°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.8°2θ, 25.4°2θ, 18.2°2θ,9.1°2θ, 22.3°2θ, 27.3°2θ, and 17.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.8°2θ, 25.4°2θ, 18.2°2θ, 9.1°2θ,22.3°2θ, 27.3°2θ, and 17.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#1 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, or twenty-one XRPD signalsselected from those set forth in Table 41.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 16.7°2θ, 16.4°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #3 characterized by XRPD signals at 16.7°2θ, 16.4°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 16.7°2θ, 16.4°2θ, 25.5°2θ, 9.1°2θ, and 20.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #3 characterized by XRPD signals 16.7°2θ, 16.4°2θ,25.5°2θ, 9.1°2θ, and 20.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 16.7°2θ, 16.4°2θ, 25.5°2θ, 9.1°2θ, 20.1°2θ, 17.0 °2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by XRPDsignals of 16.7°2θ, 16.4°2θ, 25.5°2θ, 9.1°2θ, 20.1°2θ, 17.0°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 16.7°2θ, 16.4°2θ, 25.5°2θ, 9.1°2θ, 20.1°2θ, 17.0 °2θ,26.1°2θ, 22.4°2θ, 18.8°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by XRPDsignals at 16.7°2θ, 16.4°2θ, 25.5°2θ, 9.1°2θ, 20.1°2θ, 17.0°2θ, 26.1°2θ,22.4°2θ, 18.8°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#3 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, or twenty-four XRPD signals selected from those set forthin Table 42.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 16.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid formtabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #3 characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and16.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, and 22.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #3 characterized by XRPD signals 25.5°2θ, 16.3°2θ,16.6°2θ, 20.1°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, 22.3°2θ, 26.1°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by XRPDsignals of 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, 22.3°2θ, 26.1°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, 22.3°2θ, 26.1°2θ,26.8°2θ, 18.8°2θ, 22.5°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #3 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, 22.3°2θ, 26.1°2θ,26.8°2θ, 18.8°2θ, 22.5°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#3 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, or twenty-four XRPD signals selected from those set forthin Table 43.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.8°2θ, 16.6°2θ, and 19.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #4b is crystalline tabernanthalog monofumarate is crystallinetabernanthalog monofumarate pattern #4b characterized by XRPD signals at25.8°2θ, 16.6°2θ, and 19.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.8°2θ, 16.6°2θ, 19.5°2θ, 9.3°2θ, and 18.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #4b characterized by XRPD signals 25.8°2θ, 16.6°2θ,19.5°2θ, 9.3°2θ, and 18.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.8°2θ, 16.6°2θ, 19.5°2θ, 9.3°2θ, 18.3°2θ, 27.1°2θ, and17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized byXRPD signals of 25.8°2θ, 16.6°2θ, 19.5°2θ, 9.3°2θ, 18.3°2θ, 27.1°2θ, and17.0 °2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.8°2θ, 16.6°2θ, 19.5°2θ, 9.3°2θ, 18.3°2θ, 27.1°2θ,17.0°2θ, 22.6°2θ, 27.5°2θ, and 21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized byXRPD signals at 25.8°2θ, 16.6°2θ, 19.5°2θ, 9.3°2θ, 18.3°2θ, 27.1°2θ,17.0°2θ, 22.6°2θ, 27.5°2θ, and 21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#4b is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, or twenty XRPD signals selected fromthose set forth in Table 44.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 8.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate pattern #4bcharacterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 8.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 8.3°2θ, 9.1°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #4b characterized by XRPD signals 25.5°2θ, 16.3°2θ,8.3°2θ, 9.1°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 8.3°2θ, 9.1°2θ, 19.3°2θ, 18.1°2θ, and17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized byXRPD signals of 25.5°2θ, 16.3°2θ, 8.3°2θ, 9.1°2θ, 19.3°2θ, 18.1°2θ, and17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 8.3°2θ, 9.1°2θ, 19.3°2θ, 18.1°2θ,17.2°2θ, 16.7°2θ, 26.8°2θ, and 11.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4b characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 8.3°2θ, 9.1°2θ, 19.3°2θ, 18.1°2θ,17.2°2θ, 16.7°2θ, 26.8°2θ, and 11.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#4b is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, or twenty-one XRPD signalsselected from those set forth in Table 45.

In some embodiments, the solid form of tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate pattern #5 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 16.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog hemifumarate is crystalline tabernanthalog hemifumaratepattern #5 characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and16.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate pattern #5 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 16.9°2θ, 21.4°2θ, and 8.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate is crystalline tabernanthaloghemifumarate pattern #5 characterized by XRPD signals of 25.5°2θ,16.3°2θ, 16.9°2θ, 21.4°2θ, and 8.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate pattern #5 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 16.9°2θ, 21.4°2θ, 8.3°2θ, 11.1°2θ, and23.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate pattern #5 characterized by XRPDsignals of 25.5°2θ, 16.3°2θ, 16.9°2θ, 21.4°2θ, 8.3°2θ, 11.1°2θ, and23.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate pattern #5 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 16.9°2θ, 21.4°2θ, 8.3°2θ, 11.1°2θ,23.6°2θ, 20.0°2θ, 15.4°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form tabernanthalog hemifumarate iscrystalline tabernanthalog hemifumarate pattern #5 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 16.9°2θ, 21.4°2θ, 8.3°2θ, 11.1°2θ, 23.6°2θ,20.0°2θ, 15.4°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline crystalline tabernanthaloghemifumarate pattern #5 is characterized by one, two, three, four, five,six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen,fifteen, sixteen, seventeen, eighteen, or nineteen XRPD signals selectedfrom those set forth in Table 46.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 8.2°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate pattern #4acharacterized by XRPD signals at 25.6°2θ, 8.2°2θ, and 16.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 8.2°2θ, 16.3°2θ, 11.3°2θ, and 17.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #4a characterized by XRPD signals of 25.6°2θ,8.2°2θ, 16.3°2θ, 11.3°2θ, and 17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 8.2°2θ, 16.3°2θ, 11.3°2θ, 17.2°2θ, 21.6°2θ, and23.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized byXRPD signals of 25.6°2θ, 8.2°2θ, 16.3°2θ, 11.3°2θ, 17.2°2θ, 21.6°2θ, and23.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 8.2°2θ, 16.3°2θ, 11.3°2θ, 17.2°2θ, 21.6°2θ,23.9°2θ, 9.1°2θ, 20.4°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized byXRPD signals at 25.6°2θ, 8.2°2θ, 16.3°2θ, 11.3°2θ, 17.2°2θ, 21.6°2θ,23.9°2θ, 9.1°2θ, 20.4°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#4a is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, or twenty-two XRPDsignals selected from those set forth in Table 47.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2d characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, and 22.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #2d characterized by XRPD signals at 25.6°2θ, 16.3°2θ, and22.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2d characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 22.2°2θ, 26.0°2θ, and 25.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #2d characterized by XRPD signals of 25.6°2θ,16.3°2θ, 22.2°2θ, 26.0°2θ, and 25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2d characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 22.2°2θ, 26.0°2θ, 25.3°2θ, 20.0 °2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2d characterized byXRPD signals of 25.6°2θ, 16.3°2θ, 22.2°2θ, 26.0°2θ, 25.3°2θ, 20.0°2θ,and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2d characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 22.2°2θ, 26.0°2θ, 25.3°2θ, 20.0 °2θ,9.1°2θ, 26.9°2θ, 21.2°2θ, and 17.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2d characterized byXRPD signals at 25.6°2θ, 16.3°2θ, 22.2°2θ, 26.0°2θ, 25.3°2θ, 20.0°2θ,9.1°2θ, 26.9°2θ, 21.2°2θ, and 17.6°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#2d is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signalsselected from those set forth in Table 48.

In some embodiments, the solid form of tabernanthalog monofumaratepattern #2b is crystalline tabernanthalog monofumarate pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate pattern #2b is crystallinetabernanthalog monofumarate pattern #2b characterized by XRPD signals at25.5°2θ, 16.3°2θ, and 26.8 (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumaratepattern #2b is crystalline tabernanthalog monofumarate pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 26.8°2θ, 18.0°2θ, and9.0°2θ°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate pattern #2bis crystalline tabernanthalog monofumarate pattern #2b characterized byXRPD signals of 25.5°2θ, 16.3°2θ, 26.8°2θ, 18.0°2θ, and 9.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratepattern #2b is crystalline tabernanthalog monofumarate pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 26.8°2θ, 18.0°2θ, 9.0°2θ, 25.1°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate pattern #2b is crystalline tabernanthalog monofumaratepattern #2b characterized by XRPD signals of 25.5°2θ, 16.3°2θ, 26.8°2θ,18.0°2θ, 9.0°2θ, 25.1°2θ, and 22.1 (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumaratepattern #2b is crystalline tabernanthalog monofumarate pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 26.8°2θ, 18.0°2θ, 9.0°2θ, 25.1°2θ, 22.1°2θ, 22.5°2θ, 17.4°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate pattern #2b is crystalline tabernanthalogmonofumarate pattern #2b characterized by XRPD signals at 25.5°2θ,16.3°2θ, 26.8°2θ, 18.0°2θ, 9.0°2θ, 25.1°2θ, 22.1°2θ, 22.5°2θ, 17.4°2θ,and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#2b is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, or thirteen XRPD signals selected from thoseset forth in Table 49.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #1 characterized by XRPD signals at 25.6°2θ, 16.4°2θ, and19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, and 18.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #1 characterized by XRPD signals of 25.6°2θ,16.4°2θ, 19.4°2θ, 16.8°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 18.2°2θ, 22.4°2θ, and26.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 18.2°2θ, 22.4°2θ, and26.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 18.2°2θ, 22.4°2θ,26.9°2θ, 27.3°2θ, 26.9°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 18.2°2θ, 22.4°2θ,26.9°2θ, 27.3°2θ, 26.9°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#1 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, orseventeen XRPD signals selected from those set forth in Table 50.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #1 characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and 18.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #1 characterized by XRPD signals of 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ,27.2°2θ, 22.3°2θ, 26.8°2θ, and 6.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #1 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, 27.2°2θ,22.3°2θ, 26.8°2θ, and 6.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#1 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, orseventeen XRPD signals selected from those set forth in Table 51.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #8 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 15.9°2θ, 16.4°2θ, and 25.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #8 characterized by XRPD signals at 15.9°2θ, 16.4°2θ, and25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #8 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 15.9°2θ, 16.4°2θ, 25.6°2θ, 24.3°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #8 characterized by XRPD signals of 15.9°2θ,16.4°2θ, 25.6°2θ, 24.3°2θ, and 20.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #8 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 15.9°2θ, 16.4°2θ, 25.6°2θ, 24.3°2θ, 20.6°2θ, 7.6°2θ, and19.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #8 characterized by XRPDsignals 15.9°2θ, 16.4°2θ, 25.6°2θ, 24.3°2θ, 20.6°2θ, 7.6°2θ, and19.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #8 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 15.9°2θ, 16.4°2θ, 25.6°2θ, 24.3°2θ, 20.6°2θ, 7.6°2θ,19.1°2θ, 20.8°2θ, 9.1°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #8 characterized by XRPDsignals at 15.9°2θ, 16.4°2θ, 25.6°2θ, 24.3°2θ, 20.6°2θ, 7.6°2θ, 19.1°2θ,20.8°2θ, 9.1°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#8 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, orseventeen XRPD signals selected from those set forth in Table 52.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, and 11.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #4a characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and11.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 11.3°2θ, 8.2°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #4a characterized by XRPD signals 25.5°2θ, 16.3°2θ,11.3°2θ, 8.2°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting 25.5°2θ, 16.3°2θ, 11.3°2θ, 8.2°2θ, 17.0°2θ, 21.5°2θ, and23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized byXRPD signals 25.5°2θ, 16.3°2θ, 11.3°2θ, 8.2°2θ, 17.0°2θ, 21.5°2θ, and23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.5°2θ, 16.3°2θ, 11.3°2θ, 8.2°2θ, 17.0°2θ, 21.5°2θ,23.7°2θ, 20.2°2θ, 15.6°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 11.3°2θ, 8.2°2θ, 17.0°2θ, 21.5°2θ,23.7°2θ, 20.2°2θ, 15.6°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #4a is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, or twenty-two XRPD signals selected fromthose set forth in Table 53.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #13 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.0°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratepattern #13 characterized by XRPD signals at 25.6°2θ, 16.0°2θ, and16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #13 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ, and 19.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #13 characterized by XRPD signals 25.6°2θ, 16.0°2θ,16.4°2θ, 25.0°2θ, and 19.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #13 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ, and8.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #13 characterized byXRPD signals 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ, and8.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #13 characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ,8.1°2θ, 21.9°2θ, 9.1°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate pattern #13characterized by XRPD signals at 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ,19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ;or 0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#13 is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, or nineteen XRPD signals selected from those setforth in Table 54.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate pattern #2bcharacterized by XRPD signals at 25.6°2θ, 16.3°2θ, and 9.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 9.1°2θ, 24.7°2θ, and 18.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate is crystalline tabernanthalogmonofumarate pattern #2b characterized by XRPD signals 25.6°2θ, 16.3°2θ,9.1°2θ, 24.7°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 9.1°2θ, 24.7°2θ, 18.1°2θ, 26.8°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized byXRPD signals 25.6°2θ, 16.3°2θ, 9.1°2θ, 24.7°2θ, 18.1°2θ, 26.8°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized by twoor more, or three or more XRPD signals selected from the groupconsisting of 25.6°2θ, 16.3°2θ, 9.1°2θ, 24.7°2θ, 18.1°2θ, 26.8°2θ,17.1°2θ, 17.4°2θ, 15.6°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate pattern #2b characterized byXRPD signals at 25.6°2θ, 16.3°2θ, 9.1°2θ, 24.7°2θ, 18.1°2θ, 26.8°2θ,17.1°2θ, 17.4°2θ, 15.6°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate pattern#2b is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, or eighteen XRPD signals selected from those set forth inTable 55.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, and 16.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.0°2θ, and 16.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.0°2θ, 16.4°2θ, 25°2θ, and19.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.0°2θ, 16.4°2θ, 25°2θ,19.7°2θ, 17.5°2θ, and 8.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.0°2θ, 16.4°2θ, 25°2θ,19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 56.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 16.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 16.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 16.8°2θ, 19.3°2θ, and9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 16.8°2θ, 19.3°2θ,9.0°2θ, 18.1°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 16.8°2θ, 19.3°2θ,9.0°2θ, 18.1°2θ, 22.3°2θ, 24.6°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 57.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,22.3°2θ, 22.4°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,22.3°2θ, 22.4°2θ, 26.8°2θ, 9.0°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 58.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.5°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.4°2θ, 25.5°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.4°2θ, 25.5°2θ, 19.4°2θ, 16.8°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.4°2θ, 25.5°2θ, 19.4°2θ, 16.8°2θ,9.1°2θ, 25.2°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.4°2θ, 25.5°2θ, 19.4°2θ, 16.8°2θ,9.1°2θ, 25.2°2θ, 18.2°2θ, 26.8°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 59.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #4a) is crystalline tabernanthalog monofumarate (Pattern #4a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #4a) is crystalline tabernanthalog monofumarate (Pattern #4a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #4a) is crystalline tabernanthalog monofumarate (Pattern #4a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 8.2°2θ, 9.0°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #4a) is crystalline tabernanthalog monofumarate (Pattern #4a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 8.2°2θ, 9.0°2θ,17.1°2θ, 21.5°2θ, and 23.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #4a) is crystalline tabernanthalog monofumarate (Pattern #4a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 8.2°2θ, 9.0°2θ,17.1°2θ, 21.5°2θ, 23.8°2θ, 11.2°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 60.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, and 9.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, and 9.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 9.1°2θ, 18.1°2θ, and24.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 9.1°2θ, 18.1°2θ,24.8°2θ, 26.8°2θ, and 15.5°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 9.1°2θ, 18.1°2θ,24.8°2θ, 26.8°2θ, 15.5°2θ, 22.6°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 61.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.4°2θ, and 16.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 25.5°2θ, 16.4°2θ, and 16.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 25.5°2θ, 16.4°2θ, 16.6°2θ, 22.3°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 25.5°2θ, 16.4°2θ, 16.6°2θ, 22.3°2θ,22.4°2θ, 26.0°2θ, and 20.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 25.5°2θ, 16.4°2θ, 16.6°2θ, 22.3°2θ,22.4°2θ, 26.0°2θ, 20.1°2θ, 26.7°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 62.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.0°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 26.0°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 26.0°2θ, 16.5°2θ, 20.6°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 26.0°2θ, 16.5°2θ, 20.6°2θ,25.3°2θ, 22° 20, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 26.0°2θ, 16.5°2θ, 20.6°2θ,25.3°2θ, 22°2θ, 19.3°2θ, 12.9°2θ, and 33.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 63.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #19) is crystalline tabernanthalog monofumarate (Pattern #19)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.3°2θ, 22.7°2θ, and 20.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #19) is crystalline tabernanthalog monofumarate (Pattern #19)characterized by XRPD signals at 25.3°2θ, 22.7°2θ, and 20.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #19) is crystalline tabernanthalog monofumarate (Pattern #19)characterized by XRPD signals at 25.3°2θ, 22.7°2θ, 20.5°2θ, 27.1°2θ, and16.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #19) is crystalline tabernanthalog monofumarate (Pattern #19)characterized by XRPD signals at 25.3°2θ, 22.7°2θ, 20.5°2θ, 27.1°2θ,16.5°2θ, 19.3°2θ, and 26.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #19) is crystalline tabernanthalog monofumarate (Pattern #19)characterized by XRPD signals at 25.3°2θ, 22.7°2θ, 20.5°2θ, 27.1°2θ,16.5°2θ, 19.3°2θ, 26.6°2θ, 9.1°2θ, and 16.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 64.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.7°2θ, 16.4°2θ, and 17.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.7°2θ, 16.4°2θ, and 17.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.7°2θ, 16.4°2θ, 17.2°2θ, 9.2°2θ, and23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.7°2θ, 16.4°2θ, 17.2°2θ, 9.2°2θ,23.0°2θ, 27.4°2θ, and 15.8°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate (Pattern #2a) is crystalline tabernanthalog monofumarate(Pattern #2a) characterized by XRPD signals at 25.7°2θ, 16.4°2θ,17.2°2θ, 9.2°2θ, 23.0°2θ, 27.4°2θ, 15.8°2θ, 12.4°2θ, and22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 65.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.5°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.5°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.5°2θ, 19.4°2θ, 16.7°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.5°2θ, 19.4°2θ, 16.7°2θ,18.2°2θ, 27° 20, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.5°2θ, 19.4°2θ, 16.7°2θ,18.2°2θ, 27°2θ, 27.2°2θ, 9.2°2θ, and 22.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 66.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 27.3°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 27.3°2θ, 9.1°2θ, 22.3°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 67.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.7°2θ, 25.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.7°2θ, 25.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.7°2θ, 25.6°2θ, 16.5°2θ, 16.9°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.7°2θ, 25.6°2θ, 16.5°2θ, 16.9°2θ,22.4°2θ, 20.2°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.7°2θ, 25.6°2θ, 16.5°2θ, 16.9°2θ,22.4°2θ, 20.2°2θ, 26.2°2θ, 18.9°2θ, and 26.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 68.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 22.3°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 22.3°2θ, 27.2°2θ, 26.1°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 69.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 25.4°2θ, and 16.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 25.4°2θ, and 16.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 25.4°2θ, 16.3°2θ, 19.3°2θ, and16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 25.4°2θ, 16.3°2θ, 19.3°2θ,16.1°2θ, 21.2°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 25.4°2θ, 16.3°2θ, 19.3°2θ,16.1°2θ, 21.2°2θ, 16.7°2θ, 18.1°2θ, and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 70.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #5) is crystalline tabernanthalog monofumarate (Pattern #5)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.0°2θ, 21.4°2θ, and 15.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #5) is crystalline tabernanthalog monofumarate (Pattern #5)characterized by XRPD signals at 17.0°2θ, 21.4°2θ, and 15.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #5) is crystalline tabernanthalog monofumarate (Pattern #5)characterized by XRPD signals at 17.0°2θ, 21.4°2θ, 15.4°2θ, 8.2°2θ, and23.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #5) is crystalline tabernanthalog monofumarate (Pattern #5)characterized by XRPD signals at 17.0°2θ, 21.4°2θ, 15.4°2θ, 8.2°2θ,23.6°2θ, 11.1°2θ, and 20.0°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #5) is crystalline tabernanthalog monofumarate (Pattern #5)characterized by XRPD signals at 17.0°2θ, 21.4°2θ, 15.4°2θ, 8.2°2θ,23.6°2θ, 11.1°2θ, 20.0°2θ, 25.5°2θ, and 22.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 71.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.4°2θ, 24.5°2θ, and 15.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by XRPD signals at 25.4°2θ, 24.5°2θ, and 15.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by XRPD signals at 25.4°2θ, 24.5°2θ, 15.7°2θ, 16.3°2θ, and25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by XRPD signals at 25.4°2θ, 24.5°2θ, 15.7°2θ, 16.3°2θ,25.1°2θ, 19.3°2θ, and 16.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #9) is crystalline tabernanthalog monofumarate (Pattern #9)characterized by XRPD signals at 25.4°2θ, 24.5°2θ, 15.7°2θ, 16.3°2θ,25.1°2θ, 19.3°2θ, 16.9°2θ, 21.6°2θ, and 20.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 72.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,22.3°2θ, 9.0°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,22.3°2θ, 9.0°2θ, 27.2°2θ, 18.1°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 73.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.1°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.5°2θ, 16.1°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.5°2θ, 16.1°2θ, 26.8°2θ, 9.0°2θ, and25.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.5°2θ, 16.1°2θ, 26.8°2θ, 9.0°2θ,25.2°2θ, 18.0°2θ, and 21.2°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2b) is crystalline tabernanthalog monofumarate (Pattern #2b)characterized by XRPD signals at 25.5°2θ, 16.1°2θ, 26.8°2θ, 9.0°2θ,25.2°2θ, 18.0°2θ, 21.2°2θ, 17.4°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 74.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ,22.4°2θ, 18.2°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ,22.4°2θ, 18.2°2θ, 9.1°2θ, 26.9°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 75.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ,18.2°2θ, 9.1°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ,18.2°2θ, 9.1°2θ, 22.4°2θ, 27.3°2θ, and 26.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 76.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 26.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 26.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 26.7°2θ, 16.9°2θ, and27.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 26.7°2θ, 16.9°2θ,27.1°2θ, 18.0°2θ, and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 26.7°2θ, 16.9°2θ,27.1°2θ, 18.0°2θ, 9.0°2θ, 25.0°2θ, and 29.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 77.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 17.0°2θ, 26.7°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 17.0°2θ, 26.7°2θ,27.2°2θ, 9.0°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 17.0°2θ, 26.7°2θ,27.2°2θ, 9.0°2θ, 18.0°2θ, 22.9°2θ, and 25.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 78.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate (Pattern #1) is crystallinetabernanthalog monofumarate (Pattern #1) characterized by XRPD signalsat 25.5°2θ, 16.3°2θ, 19.3°2θ, 9.0°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 9.0°2θ,16.7°2θ, 18.1°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 9.0°2θ,16.7°2θ, 18.1°2θ, 26.8°2θ, 27.2°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 79.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 26.8°2θ, 9.1°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 26.8°2θ, 9.1°2θ,27.2°2θ, 17.0°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 25.6°2θ, 16.3°2θ, 26.8°2θ, 9.1°2θ,27.2°2θ, 17.0°2θ, 18.1°2θ, 14.2°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 80.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 17.0°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 16.3°2θ, 17.0°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 16.3°2θ, 17.0°2θ, 22.9°2θ, 25.5°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 15.6°2θ, 16.3°2θ, 17.0°2θ, 22.9°2θ,24.8°2θ, 25.5°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 9.1°2θ, 15.6°2θ, 16.3°2θ, 17.0°2θ,18.1°2θ, 20.6°2θ, 22.9°2θ, 24.8°2θ, 25.5°2θ, and 27.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2a) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 81.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 24.8°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate salt (Pattern#7) characterized by XRPD signals at 16.3°2θ, 24.8°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by XRPD signals at 9.1°2θ, 15.9°2θ, 16.3°2θ, 24.8°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by XRPD signals at 9.1°2θ, 15.9°2θ, 16.3°2θ, 18.1°2θ,19.3°2θ, 24.8°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #7) is crystalline tabernanthalog monofumarate (Pattern #7)characterized by XRPD signals at 9.1°2θ, 15.9°2θ, 16.3°2θ, 18.1°2θ,19.3°2θ, 19.7°2θ, 21.2°2θ, 24.8°2θ, 25.5°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #7) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 82.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 17.0°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 16.3°2θ, 17.0°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 16.3°2θ, 17.0°2θ, 22.9°2θ, 25.5°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 9.0°2θ, 15.6°2θ, 16.3°2θ, 17.0°2θ,22.9°2θ, 25.5°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2a) is crystalline tabernanthalog monofumarate (Pattern #2a)characterized by XRPD signals at 9.0°2θ, 15.6°2θ, 16.3°2θ, 17.0°2θ,18.0°2θ, 20.6°2θ, 22.9°2θ, 25.5°2θ, 26.8°2θ, and 27.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2a) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 83.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.8°2θ, 21.3.°2θ, and 23.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by XRPD signals at 16.8°2θ, 21.3.°2θ, and 23.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by XRPD signals at 16.8°2θ, 19.8°2θ, 21.3°2θ, 23.4°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by XRPD signals at 15.2°2θ, 16.8°2θ, 19.8°2θ, 21.3°2θ,23.4°2θ, 23.6°2θ, and 25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #10) is crystalline tabernanthalog monofumarate (Pattern #10)characterized by XRPD signals at 8.2°2θ, 10.9°2θ, 15.2°2θ, 16.8°2θ,19.8°2θ, 21.3°2θ, 21.8°2θ, 23.4°2θ, 23.6°2θ, and 25.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #10) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, or nineteen XRPD signals selected fromthose set forth in Table 84.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 7.4°2θ, 16.1°2θ, and 20.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by XRPD signals at 7.4°2θ, 16.1°2θ, and 20.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by XRPD signals at 7.4°2θ, 16.1°2θ, 20.2°2θ, 21.5°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by XRPD signals at 7.4°2θ, 16.1°2θ, 20.2°2θ, 21.5°2θ,25.1°2θ, 25.5°2θ, and 25.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #11) is crystalline tabernanthalog monofumarate (Pattern #11)characterized by XRPD signals at 7.4°2θ, 16.1°2θ, 17.2°2θ, 20.2°2θ,20.7°2θ, 21.5°2θ, 22.6°2θ, 25.1°2θ, 25.5°2θ, and 25.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #11) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, thirteen, fourteen, fifteen, or sixteenXRPD signals selected from those set forth in Table 85.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.2°2θ, 19.2°2θ, and 25.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.2°2θ, 19.2°2θ, and 25.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.2°2θ, 19.2°2θ, 22.1°2θ, 25.4°2θ, and27.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.2°2θ, 19.2°2θ, 22.1°2θ, 25.4°2θ,25.9°2θ, 26.7°2θ, and 27.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.2°2θ, 18.0°2θ, 19.2°2θ, 20.0°2θ,22.1°2θ, 22.3°2θ, 25.4°2θ, 25.9°2θ, 26.7°2θ, and 27.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 86.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 25.9°2θ, and 25.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 19.5°2θ, 25.9°2θ, and 25.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 19.5°2θ, 25.2°2θ, 25.9°2θ, 26.1°2θ, and28.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 13.0°2θ, 19.3°2θ, 19.5°2θ, 25.2°2θ,25.9°2θ, 26.1°2θ, and 28.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 13.0°2θ, 16.6°2θ, 19.3°2θ, 19.5°2θ,25.2°2θ, 25.9°2θ, 26.1°2θ, 28.3°2θ, 33.7°2θ, and 37.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #8) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 87.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 20.6°2θ, and 25.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, and 25.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 16.5°2θ, 19.5°2θ, 20.6°2θ, 25.2°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 16.5°2θ, 19.2°2θ, 19.5°2θ, 20.6°2θ,22.0°2θ, 25.2°2θ, and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 12.9°2θ, 16.5°2θ, 19.2°2θ, 19.5°2θ,20.6°2θ, 22.0°2θ, 25.2°2θ, 26.0°2θ, 28.0°2θ, and 33.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 88.

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of9.1°2θ, 16.3°2θ, and 25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 9.1°2θ, 16.3°2θ, and 25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 9.1°2θ, 16.3°2θ, 25.1°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog fumarate salt ischaracterized by one, two, three, or four XRPD signals selected fromthose set forth in Table 90.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 9.1°2θ, 16.3°2θ, and 25.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, and 25.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, 19.5°2θ, 25.1°2θ, and25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 14.2°2θ, 16.3°2θ, 18.1°2θ,19.5°2θ, 25.1°2θ, and 25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 14.2°2θ, 16.3°2θ, 17.5°2θ,18.1°2θ, 19.5°2θ, 25.1°2θ, 25.6°2θ, 26.1°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 91.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 19.4°2θ, and 25.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.4°2θ, 19.4°2θ, and 25.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.4°2θ, 16.8°2θ, 18.2°2θ, 19.4°2θ, and25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.4°2θ, 16.8°2θ, 18.2°2θ, 19.4°2θ,22.4°2θ, 25.6°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 9.1°2θ, 16.4°2θ, 16.8°2θ, 17.8°2θ,18.2°2θ, 19.4°2θ, 22.4°2θ, 25.6°2θ, 26.9°2θ, and 27.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 92.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 19.3°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.3°2θ, 19.3°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.3°2θ, 16.7°2θ, 19.3°2θ, 25.5°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 16.3°2θ, 16.7°2θ, 18.1°2θ, 19.3°2θ,22.3°2θ, 25.5°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 9.0°2θ, 16.3°2θ, 16.7°2θ, 18.1°2θ,19.3°2θ, 22.3°2θ, 23.1°2θ, 25.5°2θ, 26.8°2θ, and 27.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 93.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 15.8°2θ, 24.2°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 15.8°2θ, 24.2°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 15.8°2θ, 16.3°2θ, 20.6°2θ, 24.2°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 7.6°2θ, 15.8°2θ, 16.3°2θ, 19.1°2θ,20.6°2θ, 24.2°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 7.6°2θ, 9.1°2θ, 15.8°2θ, 16.3°2θ,19.1°2θ, 20.6°2θ, 21.9°2θ, 23.8°2θ, 24.2°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #8) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen orsixteen XRPD signals selected from those set forth in Table 94.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 15.9°2θ, 24.3°2θ, and 25.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 15.9°2θ, 24.3°2θ, and 25.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 15.9°2θ, 16.3°2θ, 20.6°2θ, 24.3°2θ, and25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 7.6°2θ, 15.9°2θ, 16.3°2θ, 19.1°2θ,20.6°2θ, 24.3°2θ, and 25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #8) is crystalline tabernanthalog monofumarate (Pattern #8)characterized by XRPD signals at 7.6°2θ, 9.0 °2θ, 15.9°2θ, 16.3°2θ,18.0°2θ, 19.1°2θ, 20.6°2θ, 24.3°2θ, 25.6°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #8) is characterized by one, two, three, four, five, six,seven, eight, nine, ten eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen or nineteen XRPD signals selected fromthose set forth in Table 95.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 16.6°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.3°2θ, 16.6°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.3°2θ, 16.6°2θ, 20.1°2θ, 25.5°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.3°2θ, 16.6°2θ, 18.7°2θ, 20.1°2θ,22.2°2θ, 25.5°2θ, and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 9.0°2θ, 16.3°2θ, 16.6°2θ, 16.8°2θ,18.7°2θ, 20.1°2θ, 22.2°2θ, 25.5°2θ, 26.0°2θ, and 26.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #3) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 96.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 16.6°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.3°2θ, 16.6°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.3°2θ, 16.6°2θ, 20.1°2θ, 25.5°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 16.3°2θ, 16.6°2θ, 18.8°2θ, 20.1°2θ,22.2°2θ, 25.5°2θ, and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #3) is crystalline tabernanthalog monofumarate (Pattern #3)characterized by XRPD signals at 11.1°2θ, 16.3°2θ, 16.6°2θ, 16.9°2θ,18.8°2θ, 20.1°2θ, 22.2°2θ, 25.5°2θ, 26.0°2θ, and 26.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline monofumarate (Pattern #3) ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten XRPD signals selected from those set forth in Table 97.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 9.1°2θ, 16.3°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, 20.6°2θ, 25.1°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, 19.4°2θ, 20.6°2θ,25.1°2θ, 25.5°2θ, and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 14.2°2θ, 16.3°2θ, 19.4°2θ,20.6°2θ, 21.9°2θ, 22.2°2θ, 25.1°2θ, 25.5°2θ, and 26.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 98.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 9.1°2θ, 16.3°2θ, and 19.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, and 19.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, 19.5°2θ, 25.6°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, 16.4°2θ, 19.5°2θ,25.2°2θ, 25.6°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 12.9°2θ, 14.2°2θ, 16.3°2θ,16.4°2θ, 19.5°2θ, 22.0°2θ, 25.2°2θ, 25.6°2θ, and 26.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 99.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 9.1°2θ, 19.4°2θ, and 26.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 19.4°2θ, and 26.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, 19.4°2θ, 25.5°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 12.9°2θ, 16.3°2θ, 19.4°2θ,20.6°2θ, 25.5°2θ, and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 12.9°2θ, 14.2°2θ, 16.3°2θ,19.4°2θ, 20.6°2θ, 21.9°2θ, 25.1°2θ, 25.5°2θ, and 26.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 100.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.4°2θ, 25.6°2θ, and 26.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 19.4°2θ, 25.6°2θ, and 26.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 12.9°2θ, 16.3°2θ, 19.4°2θ, 25.6°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 12.9°2θ, 16.3°2θ, 17.4°2θ,19.4°2θ, 25.6°2θ, and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 12.9°2θ, 16.3°2θ, 17.4°2θ,19.4°2θ, 25.6°2θ, 26.0°2θ, 26.8°2θ, and 31.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, or nine XRPD signals selected from those set forth inTable 101.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 9.1°2θ, 16.3°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 16.3°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 14.2°2θ, 16.3°2θ, 25.0°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 14.2°2θ, 16.3°2θ, 22.2°2θ,25.0°2θ, 25.5°2θ, and 26.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.1°2θ, 14.2°2θ, 16.3°2θ, 19.5°2θ,21.9°2θ, 22.2°2θ, 25.0°2θ, 25.5°2θ, 26.1°2θ, and 26.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 102.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 9.2°2θ, 16.5°2θ, and 25.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.2°2θ, 16.5°2θ, and 25.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.2°2θ, 16.5°2θ, 18.3°2θ, 25.4°2θ, and25.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.2°2θ, 14.4°2θ, 16.5°2θ, 18.3°2θ,25.4°2θ, 25.7°2θ, and 27.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #2c) is crystalline tabernanthalog monofumarate (Pattern #2c)characterized by XRPD signals at 9.2°2θ, 14.4°2θ, 16.5°2θ, 18.3°2θ,22.3°2θ, 22.4°2θ, 22.5°2θ, 25.4°2θ, 25.7°2θ, and 27.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #2c) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 103.

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #22) is crystalline tabernanthalog hemifumarate (Pattern #22)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 10.5°2θ, 18.9°2θ, and 27.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #22) is crystalline tabernanthalog hemifumarate (Pattern #22)characterized by XRPD signals at 10.5°2θ, 18.9°2θ, and 27.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #22) is crystalline tabernanthalog hemifumarate (Pattern #22)characterized by XRPD signals at 10.5°2θ, 15.1°2θ, 18.9°2θ, and27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate(Pattern #22) is characterized by one, two, three, or four XRPD signalsselected from those set forth in Table 105.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 25.3°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, 16.5°2θ, 20.6°2θ, and19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, 16.5°2θ, 20.6°2θ,19.4°2θ, 26°2θ, and 22.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, 16.5°2θ, 20.6°2θ,19.4°2θ, 26°2θ, 22.0°2θ, 33.4° 20, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, or nine XRPD signals selected from those set forth inTable 107.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 20.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 25.3°2θ, and19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 25.3°2θ,19.4°2θ, 26.0°2θ, and 22.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 Insome embodiments, the solid form of tabernanthalog monofumarate (Pattern#6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 25.3°2θ,19.4°2θ, 26.0°2θ, 22.0°2θ, 33.5°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, or nine XRPD signals selected from those set forth inTable 108.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 20.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 25.2°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 25.2°2θ,26.0 (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.1°2θ, 19.5°2θ, 20.6°2θ, 16.5°2θ,25.2°2θ, 26.0°2θ, 22.0°2θ, and 33.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, nine, ten or eleven XRPD signals selected from those setforth in Table 109.

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 25.5°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 25.5°2θ, and 17.0°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 25.5°2θ, 17.0 °2θ, 16.2°2θ, and21.4°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 25.5°2θ, 17.0 °2θ, 16.2°2θ,21.4°2θ, 11.2°2θ, and 23.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 25.5°2θ, 17.0 °2θ, 16.2°2θ,21.4°2θ, 11.2°2θ, 23.6°2θ, 20.2°2θ, 19.2°2θ, and 15.5°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate(Pattern #5) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, ortwenty-eight XRPD signals selected from those set forth in Table 110.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, and 20.6°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 26.1°2θ, and 20.6°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 26.1°2θ, 20.6°2θ, 16.5°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 26.1°2θ, 20.6°2θ, 16.5°2θ,25.3°2θ, 13.0°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 26.1°2θ, 20.6°2θ, 16.5°2θ,25.3°2θ, 13.0°2θ, 22.1°2θ, and 8.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6b) is characterized by one, two, three, four, five, six,seven, or eight XRPD signals selected from those set forth in Table 111.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, and 25.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, and 25.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 25.2°2θ, 20.6°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 25.2°2θ, 20.6°2θ,26.0°2θ, 22.0°2θ, and 33.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 Insome embodiments, the solid form of tabernanthalog monofumarate (Pattern#6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 25.2°2θ, 20.6°2θ,26.0°2θ, 22.0°2θ, 33.4°2θ, 37.7°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, or nine XRPD signals selected from those set forth inTable 112.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 25.5°2θ, and 16.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 25.5°2θ, and 16.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 25.5°2θ, 16.4°2θ, 16.5°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 25.5°2θ, 16.4°2θ, 16.5°2θ,9.1°2θ, 19.4°2θ, and 17.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #1) is crystalline tabernanthalog monofumarate (Pattern #1)characterized by XRPD signals at 25.6°2θ, 25.5°2θ, 16.4°2θ, 16.5°2θ,9.1°2θ, 19.4°2θ, 17.4°2θ, 22.6°2θ, 14.3°2θ, and 18.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #1) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, and nineteen XRPD signals selected fromthose set forth in Table 113.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 25.3°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, 16.5°2θ, 20.6°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, 16.5°2θ, 20.6°2θ,26.0°2θ, 12.9°2θ, and 22.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 25.3°2θ, 16.5°2θ, 20.6°2θ,26.0°2θ, 12.9°2θ, 22.0°2θ, and 31.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, or eight XRPD signals selected from those set forth in Table 114.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 8.2°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 8.2°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 8.2°2θ, 20.6°2θ, 16.5°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 8.2°2θ, 20.6°2θ, 16.5°2θ,25.3°2θ, 26.0°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6b) is crystalline tabernanthalog monofumarate (Pattern #6b)characterized by XRPD signals at 19.5°2θ, 8.2°2θ, 20.6°2θ, 16.5°2θ,25.3°2θ, 26.0°2θ, 12.9°2θ, 22.0°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6b) is characterized by one, two, three, four, five, six,seven, eight, or nine XRPD signals selected from those set forth inTable 115.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ,26.0°2θ, 22.0°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 Insome embodiments, the solid form of tabernanthalog monofumarate (Pattern#6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ,26.0°2θ, 22.0°2θ, 12.9°2θ, 33.5°2θ, and 28.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, nine or ten XRPD signals selected from those set forth inTable 116.

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 11.3°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 11.3°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 11.3°2θ, 17.0 °2θ, 21.5°2θ, and20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 11.3°2θ, 17.0 °2θ, 21.5°2θ,20.2°2θ, 23.7°2θ, and 15.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 11.3°2θ, 17.0 °2θ, 21.5°2θ,20.2°2θ, 23.7°2θ, 15.5°2θ, 22.6°2θ, 24.4°2θ, and 19.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate(Pattern #5) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, and fifteenXRPD signals selected from those set forth in Table 117.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 20.6°2θ, and 25.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, and 25.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 25.3°2θ, 16.5°2θ, and19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 25.3°2θ, 16.5°2θ,19.4°2θ, 26.0°2θ, and 22.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 20.6°2θ, 25.3°2θ, 16.5°2θ,19.4°2θ, 26.0°2θ, 22.0°2θ, 39.6°2θ, 33.4°2θ, and 28.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven or twelve XRPD signals selected fromthose set forth in Table 118.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.5°2θ, 19.5°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 16.5°2θ, 19.5°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 16.5°2θ, 19.5°2θ, 20.6°2θ, 25.3°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 16.5°2θ, 19.5°2θ, 20.6°2θ, 25.3°2θ,26.1°2θ, 20.1°2θ, and 16.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 16.5°2θ, 19.5°2θ, 20.6°2θ, 25.3°2θ,26.1°2θ, 20.1°2θ, 16.9°2θ, 19.2°2θ, 22.2°2θ, and 22.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, eighteen, or nineteen XRPD signals selected fromthose set forth in Table 119.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 16.6°2θ, and 20.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.6°2θ, 16.6°2θ, and 20.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ,26.1°2θ, 22.1°2θ, and 13.0° 2 (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ,26.1°2θ, 22.1°2θ, 13.0°2θ, and 33.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, or eight XRPD signals selected from those set forth in Table 120.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ,26.0°2θ, 22.0°2θ, and 7.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #6a) is crystalline tabernanthalog monofumarate (Pattern #6a)characterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ,26.0°2θ, 22.0°2θ, 7.5°2θ, 15.9°2θ, 33.4°2θ, and 12.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #6a) is characterized by one, two, three, four, five, six,seven, eight, nine or ten XRPD signals selected from those set forth inTable 121.

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 21.5°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 21.5°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 21.5°2θ, 17.0 °2θ, 23.7°2θ, and11.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 21.5°2θ, 17.0 °2θ, 23.7°2θ,11.3°2θ, 20.2°2θ, and 15.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate(Pattern #5) is crystalline tabernanthalog hemifumarate (Pattern #5)characterized by XRPD signals at 8.2°2θ, 21.5°2θ, 17.0 °2θ, 23.7°2θ,11.3°2θ, 20.2°2θ, 15.5°2θ, 21.3°2θ, 19.1°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate(Pattern #5) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, or eighteen XRPD signals selected from those setforth in Table 122.

1414141414141414141414 In some embodiments, the solid form oftabernanthalog fumarate salt is crystalline tabernanthalog fumarate saltcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 18.2°2θ, 9.2°2θ, and26.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.4°2θ, 19.4°2θ, 16.8°2θ, 18.2°2θ, 9.2°2θ, 26.9°2θ,27.3°2θ, 22.4°2θ, and 17.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog fumarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeenXRPD signals selected from those set forth in Table 125.

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by two or more,or three or more XRPD signals selected from the group consisting of25.6°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.3°2θ, 8.2°2θ, 17.0°2θ, and 21.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.3°2θ, 8.2°2θ, 17.0°2θ, 21.5°2θ, 23.7°2θ, and11.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog fumarate salt iscrystalline tabernanthalog fumarate salt characterized by XRPD signalsat 25.6°2θ, 16.3°2θ, 8.2°2θ, 17.0°2θ, 21.5°2θ, 23.7°2θ, 11.2°2θ,21.5°2θ, 19.5°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog fumarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three,twenty-four XRPD signals selected from those set forth in Table 126.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.2°2θ, 27.4°2θ, and 23.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.2°2θ, 27.4°2θ, and 23.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.2°2θ, 27.4°2θ, 23.0°2θ, 20.8°2θ, and15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.2°2θ, 27.4°2θ, 23.0°2θ, 20.8°2θ,15.7°2θ, 22.3°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.2°2θ, 27.4°2θ, 23.0°2θ, 20.8°2θ,15.7°2θ, 22.3°2θ, 16.1°2θ, 21.1°2θ, 24.9°2θ, and 12.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #24) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, or thirteen XRPD signalsselected from those set forth in Table 127.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.0°2θ, 15.6°2θ, and 22.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.0°2θ, 15.6°2θ, and 22.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.0°2θ, 15.6°2θ, 22.9°2θ, 20.7°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.0°2θ, 15.6°2θ, 22.9°2θ, 20.7°2θ,27.3°2θ, 15.9°2θ, and 21.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #24) is crystalline tabernanthalog monofumarate (Pattern #24)characterized by XRPD signals at 17.0°2θ, 15.6°2θ, 22.9°2θ, 20.7°2θ,27.3°2θ, 15.9°2θ, 21.0°2θ, 12.2°2θ, 24.8°2θ, and 21.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #24) is characterized by one, two, three, four, five, six,seven, eight, nine, or ten XRPD signals selected from those set forth inTable 128.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.8°2θ, 23.0°2θ, and 12.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.8°2θ, 23.0°2θ, and 12.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.8°2θ, 23.0°2θ, 12.9°2θ, 27.4°2θ, and25.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.8°2θ, 23.0°2θ, 12.9°2θ, 27.4°2θ,25.7°2θ, 16.1°2θ, and 21.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.8°2θ, 23.0°2θ, 12.9°2θ, 27.4°2θ,25.7°2θ, 16.1°2θ, 21.6°2θ, 17.1°2θ, 20.9°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #23) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen,sixteen, seventeen, or eighteen XRPD signals selected from those setforth in Table 129.

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 22.9°2θ, and 12.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.6°2θ, 22.9°2θ, and 12.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.6°2θ, 22.9°2θ, 12.8°2θ, 16.0°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.6°2θ, 22.9°2θ, 12.8°2θ, 16.0°2θ,27.3°2θ, 25.6°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate(Pattern #23) is crystalline tabernanthalog monofumarate (Pattern #23)characterized by XRPD signals at 17.6°2θ, 22.9°2θ, 12.8°2θ, 16.0°2θ,27.3°2θ, 25.6°2θ, 21.4°2θ, 16.9°2θ, 16.2°2θ, and 20.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate(Pattern #23) is characterized by one, two, three, four, five, six,seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, or fifteenXRPD signals selected from those set forth in Table 130.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.7°2θ, 17.8° 20, and 23.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at 19.7°2θ, 17.8°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.7°2θ, 17.8°2θ, 23.0°2θ, 26.3°2θ, and13.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by XRPD signals at 19.7°2θ, 17.8°2θ, 23.0°2θ, 26.3°2θ, and13.0 °2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.7°2θ, 17.8°2θ, 23.0°2θ, 26.3°2θ,13.0°2θ, 20.9°2θ, and 19.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #23 is crystalline tabernanthalog monofumaratesalt Pattern #23 characterized by XRPD signals at 19.7°2θ, 17.8°2θ,23.0°2θ, 26.3°2θ, 13.0°2θ, 20.9°2θ, and 19.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.7°2θ, 17.8°2θ, 23.0°2θ, 26.3°2θ,13.0°2θ, 20.9°2θ, 19.6°2θ, 16.1°2θ, 27.5°2θ, and 21.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at 19.7°2θ, 17.8°2θ, 23.0°2θ, 26.3°2θ, 13.0°2θ, 20.9°2θ,19.6°2θ, 16.1°2θ, 27.5°2θ, and 21.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #23 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 133.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 22.8°2θ, and 27.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at 17.6°2θ, 22.8°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 22.8°2θ, 27.2°2θ, 15.9°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by XRPD signals at 17.6°2θ, 22.8°2θ, 27.2°2θ, 15.9°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 22.8°2θ, 27.2°2θ, 15.9°2θ,21.4°2θ, 19.4°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #23 is crystalline tabernanthalog monofumaratesalt Pattern #23 characterized by XRPD signals at 17.6°2θ, 22.8°2θ,27.2°2θ, 15.9°2θ, 21.4°2θ, 19.4°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 22.8°2θ, 27.2°2θ, 15.9°2θ,21.4°2θ, 19.4°2θ, 16.2, 25.5°2θ, 12.8°2θ, and 20.7°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at 17.6°2θ, 22.8°2θ, 27.2°2θ, 15.9°2θ, 21.4°2θ, 19.4°2θ, 16.2,25.5°2θ, 12.8°2θ, and 20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #23 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 134.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 25.5°2θ, and 22.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at 17.6°2θ, 25.5°2θ, and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 25.5°2θ, 22.9°2θ, 17.0°2θ, and24.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by XRPD signals at 17.6°2θ, 25.5°2θ, 22.9°2θ, 17.0°2θ, and24.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 25.5°2θ, 22.9°2θ, 17.0°2θ,24.9°2θ, 12.8°2θ. and 21.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #23 is crystalline tabernanthalog monofumaratesalt Pattern #23 characterized by XRPD signals at 17.6°2θ, 25.5°2θ,22.9°2θ, 17.0°2θ, 24.9°2θ, 12.8°2θ, and 21.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.6°2θ, 25.5°2θ, 22.9°2θ, 17.0°2θ,24.9°2θ, 12.8°2θ, 21.0°2θ, 27.3°2θ, 21.5°2θ and 26.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at 17.6°2θ, 25.5°2θ, 22.9°2θ, 17.0°2θ, 24.9°2θ, 12.8°2θ.21.0°2θ, 27.3°2θ, 21.5°2θ, and 26.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #23 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 135.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.7°2θ, 22.9°2θ, and 16.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at 17.7°2θ, 22.9°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.7°2θ, 22.9°2θ, 16.3°2θ, 16.0°2θ, and25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by XRPD signals at 17.7°2θ, 22.9°2θ, 16.3°2θ, 16.0°2θ, and25.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.7°2θ, 22.9°2θ, 16.3°2θ, 16.0°2θ,25.6°2θ, 12.9°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #23 is crystalline tabernanthalog monofumaratesalt Pattern #23 characterized by XRPD signals at 17.7°2θ, 22.9°2θ,16.3°2θ, 16.0°2θ, 25.6°2θ, 12.9°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #23 is crystalline tabernanthalog monofumarate salt Pattern #23characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 17.7°2θ, 22.9°2θ, 16.3°2θ, 16.0°2θ,25.6°2θ, 12.9°2θ, 27.3°2θ, 21.5°2θ, 16.9°2θ, and 20.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #23 is crystallinetabernanthalog monofumarate salt Pattern #23 characterized by XRPDsignals at of 17.7°2θ, 22.9°2θ, 16.3°2θ, 16.0°2θ, 25.6°2θ, 12.9°2θ,27.3°2θ, 21.5°2θ, 16.9°2θ, and 20.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #23 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 136.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 26.2°2θ, and 20.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #6a is crystallinetabernanthalog monofumarate salt Pattern #6a characterized by XRPDsignals at 19.6°2θ, 26.2°2θ, and 20.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 26.2°2θ, 20.8°2θ, 17.1°2θ, and16.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by XRPD signals at 19.6°2θ, 26.2°2θ, 20.8°2θ, 17.1°2θ, and16.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 26.2°2θ, 20.8°2θ, 17.1°2θ,16.6°2θ, 25.4°2θ, and 13.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #6a is crystalline tabernanthalog monofumaratesalt Pattern #6a characterized by XRPD signals at 19.6°2θ, 26.2°2θ,20.8°2θ, 17.1°2θ, 16.6°2θ, 25.4°2θ, and 13.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 26.2°2θ, 20.8°2θ, 17.1°2θ,16.6°2θ, 25.4°2θ, 13.0°2θ, 23.0°2θ, 27.5°2θ, and 22.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #6a is crystallinetabernanthalog monofumarate salt Pattern #6a characterized by XRPDsignals at of 19.6°2θ, 26.2°2θ, 20.8°2θ, 17.1°2θ, 16.6°2θ, 25.4°2θ,13.0°2θ, 23.0°2θ, 27.5°2θ, and 22.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #6a is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 137.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #6a is crystallinetabernanthalog monofumarate salt Pattern #6a characterized by XRPDsignals at 19.5°2θ, 26.1°2θ, and 16.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, 16.5°2θ, 20.7°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by XRPD signals at 19.5°2θ, 26.1°2θ, 16.5°2θ, 20.7°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, 16.5°2θ, 20.7°2θ,25.3°2θ, 13.0°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #6a is crystalline tabernanthalog monofumaratesalt Pattern #6a characterized by XRPD signals at 19.5°2θ, 26.1°2θ,16.5°2θ, 20.7°2θ, 25.3°2θ, 13.0°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #6a is crystalline tabernanthalog monofumarate salt Pattern #6acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 26.1°2θ, 16.5°2θ, 20.7°2θ,25.3°2θ, 13.0°2θ, 22.1°2θ, 19.4°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #6a is crystallinetabernanthalog monofumarate salt Pattern #26a characterized by XRPDsignals at of 19.5°2θ, 26.1°2θ, 16.5°2θ, 20.7°2θ, 25.3°2θ, 13.0°2θ,22.1°2θ, 19.4°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #6a is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 138.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 9.1°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #1 is crystalline tabernanthalog monofumaratesalt Pattern #1 characterized by XRPD signals at 25.6°2θ, 16.4°2θ,19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 9.1°2θ, 26.8°2θ, 22.3°2θ, 27.3°2θ and 25.2°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 9.1°2θ, 26.8°2θ,22.3°2θ, 27.3°2θ and 25.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #1 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 140.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 26.8°2θ, 18.1°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 26.8°2θ, 18.1°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 26.8°2θ, 18.1°2θ,27.2°2θ, 25.1°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #1 is crystalline tabernanthalog monofumaratesalt Pattern #1 characterized by XRPD signals at 25.6°2θ, 16.4°2θ,26.8°2θ, 18.1°2θ, 27.2°2θ, 25.1°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 26.8°2θ, 18.1°2θ,27.2°2θ, 25.1°2θ, 22.3°2θ, 29.9°2θ, 9.1°2θ and 17.5°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, 26.8°2θ, 18.1°2θ, 27.2°2θ, 25.1°2θ,22.3°2θ, 29.9°2θ, 9.1°2θ and 17.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #1 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 141.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 9.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 9.1°2θ, 25.2°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 9.1°2θ, 25.2°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 9.1°2θ, 25.2°2θ, 26.8°2θ,16.7°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 9.1°2θ, 25.2°2θ,26.8°2θ, 16.7°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 9.1°2θ, 25.2°2θ, 26.8°2θ,16.7°2θ, 18.1°2θ, 22.4°2θ, 30.0°2θ and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, 9.1°2θ, 25.2°2θ, 26.8°2θ, 16.7°2θ, 18.1°2θ,22.4°2θ, 30.0°2θ and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #1 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 142.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.4°2θ, and 25.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 16.4°2θ, 25.4°2θ, and 25.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.4°2θ, 25.7°2θ, 9.1°2θ, and16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 16.4°2θ, 25.4°2θ, 25.7°2θ, 9.1°2θ, and16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.4°2θ, 25.7°2θ, 9.1°2θ, 16.8°2θ,19.4°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 16.4°2θ, 25.4°2θ, 25.7°2θ, 9.1°2θ,16.8°2θ, 19.4°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.4°2θ, 25.7°2θ, 9.1°2θ, 16.8°2θ,19.4°2θ, 18.2°2θ, 17.5°2θ, 26.6°2θ and 14.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 16.4°2θ, 25.4°2θ, 25.7°2θ, 9.1°2θ, 16.8°2θ, 19.4°2θ, 18.2°2θ,17.5°2θ, 26.6°2θ and 14.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #1 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 143.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 20.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the mixtureof two salts provided herein is a mixture of two crystalline saltsprovided herein characterized by XRPD signals at 25.6°2θ, 16.4°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 20.7°2θ, 17.0°2θ, and19.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals at25.6°2θ, 16.4°2θ, 20.7°2θ, 17.0°2θ, and 19.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 20.7°2θ, 17.0°2θ,19.5°2θ, 16.5°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 25.6°2θ, 16.4°2θ, 20.7°2θ, 17.0°2θ,19.5°2θ, 16.5°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 25.6°2θ, 16.4°2θ, 20.7°2θ, 17.0°2θ, 19.5°2θ, 16.5°2θ, 15.7°2θ,22.9°2θ, 27.3°2θ and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 25.6°2θ, 16.4°2θ, 20.7°2θ, 17.0°2θ,19.5°2θ, 16.5°2θ, 15.7°2θ, 22.9°2θ, 27.3°2θ and 9.1°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 144.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 20.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the mixtureof two salts provided herein is a mixture of two crystalline saltsprovided herein characterized by XRPD signals at 19.5°2θ, 20.6°2θ, and16.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ, and25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals at19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ, and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ,25.4°2θ, 25.5°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ,25.4°2θ, 25.5°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ, 25.4°2θ, 25.5°2θ, 17.0°2θ,26.0°2θ, 15.7°2θ and 22.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ,25.4°2θ, 25.5°2θ, 17.0°2θ, 26.0°2θ, 15.7°2θ and 22.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 145.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ, 25.4°2θ, 25.5°2θ, 17.0°2θ,26.1°2θ, 15.7°2θ and 22.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 20.6°2θ, 16.5°2θ, 16.4°2θ,25.4°2θ, 25.5°2θ, 17.0°2θ, 26.1°2θ, 15.7°2θ, 22.0°2θ and 9.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 146.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, and 20.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the mixtureof two salts provided herein is a mixture of two crystalline saltsprovided herein characterized by XRPD signals at 19.5°2θ, 16.5°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.5°2θ, and25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals at19.5°2θ, 16.5°2θ, 20.7°2θ, 25.5°2θ, and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.5°2θ, 25.4°2θ,17.1°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the mixture of two salts provided herein is a mixtureof two crystalline salts provided herein characterized by XRPD signalsat 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.5°2θ, 25.4°2θ, 17.1°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.5°2θ, 25.4°2θ, 17.1°2θ, 26.1°2θ,15.7°2θ, 18.1°2θ and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.5°2θ,25.4°2θ, 17.1°2θ, 26.1°2θ, 15.7°2θ, 18.1°2θ and 22.1 (±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 147.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.6°2θ, and 16.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the mixtureof two salts provided herein is a mixture of two crystalline saltsprovided herein characterized by XRPD signals at 19.5°2θ, 16.6°2θ, and16.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.6°2θ, 16.5°2θ, 20.7°2θ, and25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals at19.5°2θ, 16.6°2θ, 16.5°2θ, 20.7°2θ, and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting 19.5°2θ, 16.6°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ,25.5°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the mixture of two salts provided herein is a mixtureof two crystalline salts provided herein characterized by XRPD signalsat 19.5°2θ, 16.6°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 25.5°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consisting19.5°2θ, 16.6°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 25.5°2θ, 18.1°2θ, 26.1°2θ,17.1°2θ, and 17.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the mixture of two salts provided herein is a mixtureof two crystalline salts provided herein characterized by XRPD signalsat 19.5°2θ, 16.6°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 25.5°2θ, 18.1°2θ,26.1°2θ, 17.1°2θ, and 17.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 148.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, and 20.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the mixtureof two salts provided herein is a mixture of two crystalline saltsprovided herein characterized by XRPD signals at 19.5°2θ, 16.5°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, and25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 25.5°2θ,17.1°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the mixture of two salts provided herein is a mixtureof two crystalline salts provided herein characterized by XRPD signalsat 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 25.5°2θ, 17.1°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 25.5°2θ, 17.1°2θ, 26.1°2θ,15.7°2θ, 22.1°20 and 22.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ,25.5°2θ, 17.1°2θ, 26.1°2θ, 15.7°2θ, 22.1°20 and 22.9°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 149.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, and 20.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the mixtureof two salts provided herein is a mixture of two crystalline saltsprovided herein characterized by XRPD signals at 19.5°2θ, 16.5°2θ, and20.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.4°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals19.5°2θ, 16.5°2θ, 20.6°2θ, 25.4°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.4°2θ, 26.1°2θ,17.0°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the mixture of two salts provided herein is a mixtureof two crystalline salts provided herein characterized by XRPD signalsat 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.4°2θ, 26.1°2θ, 17.0°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.4°2θ, 26.1°2θ, 17.0°2θ, 15.7°2θ,22.1°2θ, 9.1°2θ and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.4°2θ,26.1°2θ, 17.0°2θ, 15.7°2θ, 22.1°2θ, 9.1°2θ and 12.9°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 150.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, 20.6°2θ, 16.4°2θ, and25.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals19.5°2θ, 16.5°2θ, 20.6°2θ, 16.4°2θ, and 25.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group 19.5°2θ, 16.5°2θ, 20.6°2θ, 16.4°2θ, 25.3°2θ, 25.5°2θ, and26.0 °2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals at19.5°2θ, 16.5°2θ, 20.6°2θ, 16.4°2θ, 25.3°2θ, 25.5°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.5°2θ, 16.5°2θ, 20.6°2θ, 16.4°2θ, 25.3°2θ, 25.5°2θ, 26.0°2θ,17.0°2θ, 22.0°2θ and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 16.4°2θ,25.3°2θ, 25.5°2θ, 26.0°2θ, 17.0°2θ, 22.0°2θ and 18.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 151.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 16.6°2θ, and 20.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the mixtureof two salts provided herein is a mixture of two crystalline saltsprovided herein characterized by XRPD signals at 19.6°2θ, 16.6°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ, and26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals at9.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ,26.2°2θ, 18.1°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ,26.2°2θ, 18.1°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ, 26.2°2θ, 18.1°2θ, 22.1°2θ,17.1°2θ, 17.8°2θ, and 15.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ,26.2°2θ, 18.1°2θ, 22.1°2θ, 17.1°2θ, 17.8°2θ, and 15.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 152.

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the mixture of two salts provided herein is a mixture oftwo crystalline salts provided herein characterized by XRPD signals19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 18.0°2θ,17.7°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the mixture of two salts provided herein is a mixtureof two crystalline salts provided herein characterized by XRPD signalsat 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 18.0°2θ, 17.7°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of a mixture of two salts providedherein is a mixture of two crystalline salts provided herein by two ormore, or three or more XRPD signals selected from the group consistingof 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ, 18.0°2θ, 17.7°2θ, 26.1°2θ,22.1°2θ, 22.9°2θ and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the mixture of two salts providedherein is a mixture of two crystalline salts provided hereincharacterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.7°2θ, 25.4°2θ,18.0°2θ, 17.7°2θ, 26.1°2θ, 22.1°2θ, 22.9°2θ and 12.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the a mixture of two salts provided herein is amixture of two crystalline salts provided herein is characterized byone, two, three, four, five, six, seven, eight, nine, ten, eleven,twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen,nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four,twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine,thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five,thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one,forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven,forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three,fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine,sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, orsixty-six XRPD signals selected from those set forth in Table 153.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 26.8°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #1 is crystalline tabernanthalog monofumaratesalt Pattern #1 characterized by XRPD signals at 25.5°2θ, 16.3°2θ,19.3°2θ, 16.7°2θ, 18.1°2θ, 26.8°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 26.8°2θ, 27.2°2θ, 9.0°2θ, 22.3°2θ and 25.1°2θ(±0.2°2θ; ±0.1°2θ;or 0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 26.8°2θ,27.2°2θ, 9.0°2θ, 22.3°2θ and 25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #1 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 155.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 26.8°2θ, and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #1 is crystalline tabernanthalog monofumaratesalt Pattern #1 characterized by XRPD signals at 25.5°2θ, 16.3°2θ,19.3°2θ, 16.7°2θ, 18.1°2θ, 26.8°2θ, and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,18.1°2θ, 26.8°2θ, 9.0°2θ, 22.3°2θ, 27.2°2θ and 24.6°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 26.8°2θ,9.0°2θ, 22.3°2θ, 27.2°2θ and 24.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #1 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 156.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and5.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and5.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 5.1°2θ,10.2°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,5.1°2θ, 10.2°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #1 is crystalline tabernanthalog monofumarate salt Pattern #1characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 5.1°2θ,10.2°2θ, 27.2°2θ, 18.1°2θ, 9.0°2θ and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #1 is crystallinetabernanthalog monofumarate salt Pattern #1 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 5.1°2θ, 10.2°2θ, 27.2°2θ,18.1°2θ, 9.0°2θ and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #1 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 157.

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2a is crystalline tabernanthalog monofumarate Pattern #2acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 17.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate Pattern #2a is tabernanthalogmonofumarate Pattern #2a characterized by XRPD signals at 25.6°2θ,16.4°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2a is crystalline tabernanthalog monofumarate Pattern #2acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 17.1°2θ, 9.1°2θ, and23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate Pattern #2ais crystalline tabernanthalog monofumarate Pattern #2a characterized byXRPD signals at 25.6°2θ, 16.4°2θ, 17.1°2θ, 9.1°2θ, and 23.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2a is crystalline tabernanthalog monofumarate Pattern #2acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 17.1°2θ, 9.1°2θ, 23.0°2θ, 27.3°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate Pattern #2a is crystalline tabernanthalog monofumaratePattern #2a characterized by XRPD signals at of 25.6°2θ, 16.4°2θ,17.1°2θ, 9.1°2θ, 23.0°2θ, 27.3°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2a is crystalline tabernanthalog monofumarate Pattern #2acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 17.1°2θ, 9.1°2θ, 23.0°2θ, 27.3°2θ, 15.7°2θ, 26.8°2θ, 18.1°2θ, and 20.7°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate Pattern #2a is crystalline tabernanthalogmonofumarate Pattern #2a characterized by XRPD signals at 25.6°2θ,16.4°2θ, 17.1°2θ, 9.1°2θ, 23.0°2θ, 27.3°2θ, 15.7°2θ, 26.8°2θ, 18.1°2θ,and 20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate Pattern#2a is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 158.

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2b is crystalline tabernanthalog monofumarate Pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 24.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate Pattern #2b is crystallinetabernanthalog monofumarate Pattern #2b characterized by XRPD signals at25.5°2θ, 16.3°2θ, and 24.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2b is crystalline tabernanthalog monofumarate Pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 24.6°2θ, 18.1°2θ, and9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate Pattern #2bis crystalline tabernanthalog monofumarate Pattern #2b characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 24.6°2θ, 18.1°2θ, and 9.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2b is crystalline tabernanthalog monofumarate Pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 24.6°2θ, 18.1°2θ, 9.0°2θ, 25.1°2θ, and 15.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate Pattern #2b is crystalline tabernanthalog monofumaratePattern #2b characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 24.6°2θ,18.1°2θ, 9.0°2θ, 25.1°2θ, and 15.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2b is crystalline tabernanthalog monofumarate Pattern #2bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 24.6°2θ, 18.1°2θ, 9.0°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate Pattern #2b is crystalline tabernanthalogmonofumarate Pattern #2b characterized by XRPD signals at 25.5°2θ,16.3°2θ, 24.6°2θ, 18.1°2θ, 9.0°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ,and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate Pattern#2b is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 159.

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2c is crystalline tabernanthalog monofumarate Pattern #2ccharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3° 20, and 19.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate Pattern #2c is crystallinetabernanthalog monofumarate Pattern #2c characterized by XRPD signals at25.5°2θ, 16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2c is crystalline tabernanthalog monofumarate Pattern #2ccharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate Pattern #2cis crystalline tabernanthalog monofumarate Pattern #2c characterized byXRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, and 22.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2c is crystalline tabernanthalog monofumarate Pattern #2ccharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,22.3°2θ, 9.0°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate Pattern #2c is crystalline tabernanthalog monofumaratePattern #2c characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 22.3°2θ, 9.0°2θ, and 27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2c is crystalline tabernanthalog monofumarate Pattern #2ccharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ,22.3°2θ, 9.0°2θ, 27.2°2θ, 18.1°2θ, 26.8°2θ, and 17.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate Pattern #2c is crystallinetabernanthalog monofumarate Pattern #2c characterized by XRPD signals at25.5°2θ, 16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 9.0°2θ, 27.2°2θ, 18.1°2θ,26.8°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate Pattern#2c is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 160.

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2d is crystalline tabernanthalog monofumarate Pattern #2dcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, and 16.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate Pattern #2d is crystallinetabernanthalog monofumarate Pattern #2d characterized by XRPD signals at25.6°2θ, 16.3°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2d is crystalline tabernanthalog monofumarate Pattern #2dcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, 16.2°2θ, 25.2°2θ, and9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate Pattern #2dis crystalline tabernanthalog monofumarate Pattern #2d characterized byXRPD signals at 25.6°2θ, 16.3°2θ, 16.2°2θ, 25.2°2θ, and 9.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2d is crystalline tabernanthalog monofumarate Pattern #2dcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, 16.2°2θ, 25.2°2θ, 9.1°2θ,22.1°2θ, and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate Pattern#2d is crystalline tabernanthalog monofumarate Pattern #2d characterizedby XRPD signals at 25.6°2θ, 16.3°2θ, 16.2°2θ, 25.2°2θ, 9.1°2θ, 22.1°2θ,and 26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #2d is crystalline tabernanthalog monofumarate Pattern #2dcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, 16.2°2θ, 25.2°2θ, 9.1°2θ,22.1°2θ, 26.0°2θ, 26.8°2θ, 18.1°2θ, and 19.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate Pattern #2d is crystalline tabernanthalogmonofumarate Pattern #2d characterized by XRPD signals at 25.6°2θ,16.3°2θ, 16.2°2θ, 25.2°2θ, 9.1°2θ, 22.1°2θ, 26.0°2θ, 26.8°2θ, 18.1°2θ,and 19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate Pattern#2d is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 161.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #3 is crystalline tabernanthalog monofumarate salt Pattern #3characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 16.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #3 is crystallinetabernanthalog monofumarate salt Pattern #3 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, and 16.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #3 is crystalline tabernanthalog monofumarate salt Pattern #3characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#3 is crystalline tabernanthalog monofumarate salt Pattern #3characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, and26.0 °2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #3 is crystalline tabernanthalog monofumarate salt Pattern #3characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ,26.0°2θ, 22.2°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #3 is crystalline tabernanthalog monofumaratesalt Pattern #3 characterized by XRPD signals at 25.5°2θ, 16.3°2θ,16.6°2θ, 20.1°2θ, 26.0°2θ, 22.2°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #3 is crystalline tabernanthalog monofumarate salt Pattern #3characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ,26.0°2θ, 22.2°2θ, 26.8°2θ, 16.8°2θ, 18.8°2θ, and 9.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #3 is crystallinetabernanthalog monofumarate salt Pattern #3 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 16.6°2θ, 20.1°2θ, 26.0°2θ, 22.2°2θ,26.8°2θ, 16.8°2θ, 18.8°2θ, and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #3 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 162.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4a is crystalline tabernanthalog monofumarate salt Pattern #4acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #4a is crystallinetabernanthalog monofumarate salt Pattern #4a characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4a is crystalline tabernanthalog monofumarate salt Pattern #4acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 8.2°2θ, 11.3°2θ, and9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#4a is crystalline tabernanthalog monofumarate salt Pattern #4acharacterized by XRPD signals at 25.5°2θ, 16.3°2θ, 8.2°2θ, 11.3°2θ, and9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4a is crystalline tabernanthalog monofumarate salt Pattern #4acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 8.2°2θ, 11.3°2θ, 9.0 °2θ,23.8°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #4a is crystalline tabernanthalog monofumarate salt Pattern #4acharacterized by XRPD signals at 25.5°2θ, 16.3°2θ, 8.2°2θ, 11.3°2θ,9.0°2θ, 23.8°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4a is crystalline tabernanthalog monofumarate salt Pattern #4acharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 8.2°2θ, 11.3°2θ, 9.0 °2θ,23.8°2θ, 17.1°2θ, 19.3°2θ, 19.4°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #4a is crystallinetabernanthalog monofumarate salt Pattern #4a characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 8.2°2θ, 11.3°2θ, 9.0°2θ, 23.8°2θ, 17.1°2θ,19.3°2θ, 19.4°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #4a is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 163.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4b is crystalline tabernanthalog monofumarate salt Pattern #4bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #4b is crystallinetabernanthalog monofumarate salt Pattern #4b characterized by XRPDsignals at 25.6°2θ, 16.3°2θ, and 8.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4b is crystalline tabernanthalog monofumarate salt Pattern #4bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, 8.2°2θ, 9.1°2θ, and17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#4b is crystalline tabernanthalog monofumarate salt Pattern #4bcharacterized by XRPD signals at 25.6°2θ, 16.3°2θ, 8.2°2θ, 9.1°2θ, and17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4b is crystalline tabernanthalog monofumarate salt Pattern #4bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, 8.2°2θ, 9.1°2θ, 17.2°2θ,18.1°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #4b is crystalline tabernanthalog monofumarate salt Pattern #4bcharacterized by XRPD signals at 25.6°2θ, 16.3°2θ, 8.2°2θ, 9.1°2θ,17.2°2θ, 18.1°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #4b is crystalline tabernanthalog monofumarate salt Pattern #4bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.3°2θ, 8.2°2θ, 9.1°2θ, 17.2°2θ,18.1°2θ, 26.8°2θ, 15.7°2θ, 21.5°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #4b is crystallinetabernanthalog monofumarate salt Pattern #4b characterized by XRPDsignals at 25.6°2θ, 16.3°2θ, 8.2°2θ, 9.1°2θ, 17.2°2θ, 18.1°2θ, 26.8°2θ,15.7°2θ, 21.5°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #4b is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 164.

In some embodiments, the solid form of tabernanthalog unary fumaratesalt Pattern #6a is crystalline tabernanthalog unary fumarate saltPattern #6a characterized by two or more, or three or more XRPD signalsselected from the group consisting of 19.6°2θ, 16.6°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog unary fumarate saltPattern #6a is crystalline tabernanthalog unary fumarate salt Pattern#6a characterized by XRPD signals at 19.6°2θ, 16.6°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog unary fumaratesalt Pattern #6a is crystalline tabernanthalog unary fumarate saltPattern #6a characterized by two or more, or three or more XRPD signalsselected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog unary fumarate saltPattern #6a is crystalline tabernanthalog unary fumarate salt Pattern#6a characterized by XRPD signals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ,and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog unary fumaratesalt Pattern #6a is crystalline tabernanthalog unary fumarate saltPattern #6a characterized by two or more, or three or more XRPD signalsselected from the group consisting 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ,19.3°2θ, 26.2°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalog unaryfumarate salt Pattern #6a is crystalline tabernanthalog unary fumaratesalt Pattern #6a characterized by XRPD signals at 19.6°2θ, 16.6°2θ,20.7°2θ, 25.4°2θ, 19.3°2θ, 26.2°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog unary fumaratesalt Pattern #6a is crystalline tabernanthalog unary fumarate saltPattern #6a characterized by two or more, or three or more XRPD signalsselected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, 26.2°2θ, 22.1°2θ, 33.6°2θ, and 13.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog unary fumarate salt Pattern #6ais crystallinetabernanthalog unary fumarate salt Pattern #6a characterized by XRPDsignals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.4°2θ, 19.3°2θ, 26.2°2θ,22.1°2θ, 33.6°2θ, and 13.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog unary fumarate saltPattern #6a is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 166.

In some embodiments, the solid form of tabernanthalog monofumaratePattern #6b is crystalline tabernanthalog monofumarate Pattern #6bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.4°2θ, 16.5°2θ, and 20.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate Pattern #6b is crystallinetabernanthalog monofumarate Pattern #6b characterized by XRPD signals at19.4°2θ, 16.5°2θ, and 20.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #6b is crystalline tabernanthalog monofumarate Pattern #6bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.4°2θ, 16.5°2θ, 20.5°2θ, 25.3°2θ, and26.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate Pattern #6bis crystalline tabernanthalog monofumarate Pattern #6b characterized byXRPD signals at 19.4°2θ, 16.5°2θ, 20.5°2θ, 25.3°2θ, and 26.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #6b is crystalline tabernanthalog monofumarate Pattern #6bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.4°2θ, 16.5°2θ, 20.5°2θ, 25.3°2θ,26.0°2θ, 22.0°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate Pattern #6b is crystalline tabernanthalog monofumaratePattern #6b characterized by XRPD signals at 19.4°2θ, 16.5°2θ, 20.5°2θ,25.3°2θ, 26.0°2θ, 22.0°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumaratePattern #6b is crystalline tabernanthalog monofumarate Pattern #6bcharacterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.4°2θ, 16.5°2θ, 20.5°2θ, 25.3°2θ,26.0°2θ, 22.0°2θ, 12.9°2θ, 8.2°2θ, 33.4°2θ, and 37.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate Pattern #6b is crystallinetabernanthalog monofumarate Pattern #6b characterized by XRPD signals at19.4°2θ, 16.5°2θ, 20.5°2θ, 25.3°2θ, 26.0°2θ, 22.0°2θ, 12.9°2θ, 8.2°2θ,33.4°2θ, and 37.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate Pattern#6b is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 167.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #7 is crystalline tabernanthalog monofumarate salt Pattern #7characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.6°2θ, and 15.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #7 is crystallinetabernanthalog monofumarate salt Pattern #7 characterized by XRPDsignals at 16.4°2θ, 25.6°2θ, and 15.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #7 is crystalline tabernanthalog monofumarate salt Pattern #7characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.6°2θ, 15.9°2θ, 7.2°2θ, and24.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#7 is crystalline tabernanthalog monofumarate salt Pattern #7characterized by XRPD signals at 16.4°2θ, 25.6°2θ, 15.9°2θ, 7.2°2θ, and24.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #7 is crystalline tabernanthalog monofumarate salt Pattern #7characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 16.4°2θ, 25.6°2θ, 15.9°2θ, 7.2°2θ, 24.9°2θ,19.4°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #7 is crystalline tabernanthalog monofumarate salt Pattern #7characterized by XRPD signals at 16.4°2θ, 25.6°2θ, 15.9°2θ, 7.2°2θ,24.9°2θ, 19.4°2θ, and 9.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #7 is crystalline tabernanthalog monofumarate salt Pattern #7characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.4°2θ, 25.6°2θ, 15.9°2θ, 7.2°2θ, 24.9°2θ,19.4°2θ, 9.1°2θ, 19.8°2θ, 21.3°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #7 is crystallinetabernanthalog monofumarate salt Pattern #7 characterized by XRPDsignals at 16.4°2θ, 25.6°2θ, 15.9°2θ, 7.2°2θ, 24.9°2θ, 19.4°2θ, 9.1°2θ,19.8°2θ, 21.3°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #7 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,or seventeen, XRPD signals selected from those set forth in Table 168.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #8 is crystalline tabernanthalog monofumarate salt Pattern #8characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, and 15.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #8 is crystallinetabernanthalog monofumarate salt Pattern #8 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, and 15.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #8 is crystalline tabernanthalog monofumarate salt Pattern #8characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 15.8°2θ, 24.2°2θ, and20.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#8 is crystalline tabernanthalog monofumarate salt Pattern #8characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 15.8°2θ, 24.2°2θ, and20.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #8 is crystalline tabernanthalog monofumarate salt Pattern #8characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 25.5°2θ, 16.3°2θ, 15.8°2θ, 24.2°2θ, 20.5°2θ,24.8°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #8 is crystalline tabernanthalog monofumarate salt Pattern #8characterized by XRPD signals at 25.5°2θ, 16.3°2θ, 15.8°2θ, 24.2°2θ,20.5°2θ, 24.8°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #8 is crystalline tabernanthalog monofumarate salt Pattern #8characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.3°2θ, 15.8°2θ, 24.2°2θ,20.5°2θ, 24.8°2θ, 18.0°2θ, 7.6°2θ, 9.0°2θ, and 19.0°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #8 is crystallinetabernanthalog monofumarate salt Pattern #8 characterized by XRPDsignals at 25.5°2θ, 16.3°2θ, 15.8°2θ, 24.2°2θ, 20.5°2θ, 24.8°2θ,18.0°2θ, 7.6°2θ, 9.0°2θ, and 19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #8 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, or nineteen, XRPD signals selected from those setforth in Table 169.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #9 is crystalline tabernanthalog monofumarate salt Pattern #9characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 15.9°2θ, 25.6°2θ, and 24.7°2θ(±0.2 °2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #9 is crystallinetabernanthalog monofumarate salt Pattern #9 characterized by XRPDsignals at 15.9°2θ, 25.6°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #9 is crystalline tabernanthalog monofumarate salt Pattern #9characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 15.9°2θ, 25.6°2θ, 24.7°2θ, 16.4°2θ, and19.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#9 is crystalline tabernanthalog monofumarate salt Pattern #9characterized by XRPD signals at 15.9°2θ, 25.6°2θ, 24.7°2θ, 16.4°2θ, and19.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #9 is crystalline tabernanthalog monofumarate salt Pattern #9characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 15.9°2θ, 25.6°2θ, 24.7°2θ, 16.4°2θ, 19.5°2θ,21.9°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #9 is crystalline tabernanthalog monofumarate salt Pattern #9characterized by XRPD signals at 15.9°2θ, 25.6°2θ, 24.7°2θ, 16.4°2θ,19.5°2θ, 21.9°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #9 is crystalline tabernanthalog monofumarate salt Pattern #9characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 15.9°2θ, 25.6°2θ, 24.7°2θ, 16.4°2θ,19.5°2θ, 21.9°2θ, 17.1°2θ, 8.0°2θ, 9.2°2θ, and 20.8°2θ(±0.2°2θ; ±0.1°2θ;or 0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #9 is crystallinetabernanthalog monofumarate salt Pattern #9 characterized by XRPDsignals at 15.9°2θ, 25.6°2θ, 24.7°2θ, 16.4°2θ, 19.5°2θ, 21.9°2θ,17.1°2θ, 8.0°2θ, 9.2°2θ, and 20.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #9 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, or nineteen, XRPD signals selected from those setforth in Table 170.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #10 is crystalline tabernanthalog monofumarate salt Pattern #10characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.9°2θ, and 16.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #10 is crystallinetabernanthalog monofumarate salt Pattern #10 characterized by XRPDsignals at 25.5°2θ, 16.9°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #10 is crystalline tabernanthalog monofumarate salt Pattern #10characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.9°2θ, 16.3°2θ, 21.3°2θ, and23.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#10 is crystalline tabernanthalog monofumarate salt Pattern #10characterized by XRPD signals at 25.5°2θ, 16.9°2θ, 16.3°2θ, 21.3°2θ, and23.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #10 is crystalline tabernanthalog monofumarate salt Pattern #10characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 25.5°2θ, 16.9°2θ, 16.3°2θ, 21.3°2θ, 23.5°2θ,8.2°2θ, and 10.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #10 is crystalline tabernanthalog monofumarate salt Pattern #10characterized by XRPD signals at 25.5°2θ, 16.9°2θ, 16.3°2θ, 21.3°2θ,23.5°2θ, 8.2°2θ, and 10.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #10 is crystalline tabernanthalog monofumarate salt Pattern #10characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.5°2θ, 16.9°2θ, 16.3°2θ, 21.3°2θ,23.5°2θ, 8.2°2θ, 10.8°2θ, 9.1°2θ, 23.4°2θ, and 19.8°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #10 is crystallinetabernanthalog monofumarate salt Pattern #10 characterized by XRPDsignals at 25.5°2θ, 16.9°2θ, 16.3°2θ, 21.3°2θ, 23.5°2θ, 8.2°2θ, 10.8°2θ,9.1°2θ, 23.4°2θ, and 19.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #10 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 171.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.1°2θ, 25.7°2θ, and 16.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #11 is crystallinetabernanthalog monofumarate salt Pattern #11 characterized by XRPDsignals at 16.1°2θ, 25.7°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, and20.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by XRPD signals at 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, and20.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, 20.4°2θ,7.5°2θ, and 9.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by XRPD signals at 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ,20.4°2θ, 7.5°2θ, and 9.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the crystalline tabernanthalogmonofumarate salt Pattern #10 tabernanthalog monofumarate salt Pattern#11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ,20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 17.4°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #11 is crystallinetabernanthalog monofumarate salt Pattern #11 characterized by XRPDsignals at 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ,23.9°2θ, 17.4°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #11 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, or twenty-five XRPD signals selected fromthose set forth in Table 171.

In some embodiments, the solid form of monofumarate salt Pattern #11 iscrystalline tabernanthalog monofumarate salt Pattern #11 characterizedby two or more, or three or more XRPD signals selected from the groupconsisting of 16.1°2θ, 25.7°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #11 is crystallinetabernanthalog monofumarate salt Pattern #11 characterized by XRPDsignals at 16.1°2θ, 25.7°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, and20.4°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by XRPD signals at 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, and20.4°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, 20.4°2θ,7.5°2θ, and 9.2°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by XRPD signals at 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ,20.4°2θ, 7.5°2θ, and 9.2°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #11 is crystalline tabernanthalog monofumarate salt Pattern #11characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ,20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 17.4°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #11 is crystallinetabernanthalog monofumarate salt Pattern #11 characterized by XRPDsignals at 16.1°2θ, 25.7°2θ, 16.4°2θ, 21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ,23.9°2θ, 17.4°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #11 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, orsixteen XRPD signals selected from those set forth in Table 172.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #12 is crystalline tabernanthalog monofumarate salt Pattern #12characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 25.6°2θ, and 21.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #12 is crystallinetabernanthalog monofumarate salt Pattern #12 characterized by XRPDsignals at 16.3°2θ, 25.6°2θ, and 21.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #12 is crystalline tabernanthalog monofumarate salt Pattern #12characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 25.6°2θ, 21.6°2θ, 20.3°2θ, and8.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#12 is crystalline tabernanthalog monofumarate salt Pattern #12characterized by XRPD signals at 16.3°2θ, 25.6°2θ, 21.6°2θ, 20.3°2θ, and8.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #12 is crystalline tabernanthalog monofumarate salt Pattern #12characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 16.3°2θ, 25.6°2θ, 21.6°2θ, 20.3°2θ, 8.3°2θ,9.1°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #12 is crystalline tabernanthalog monofumarate salt Pattern #12characterized by XRPD signals at 16.3°2θ, 25.6°2θ, 21.6°2θ, 20.3°2θ,8.3°2θ, 9.1°2θ, and 18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #12 is crystalline tabernanthalog monofumarate salt Pattern #12characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.3°2θ, 25.6°2θ, 21.6°2θ, 20.3°2θ, 8.3°2θ,9.1°2θ, 18.2°2θ, 23.0°2θ, 10.8°2θ, and 14.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #12 is crystallinetabernanthalog monofumarate salt Pattern #12 characterized by XRPDsignals at 16.3°2θ, 25.6°2θ, 21.6°2θ, 20.3°2θ, 8.3°2θ, 9.1°2θ, 18.2°2θ,23.0°2θ, 10.8°2θ, and 14.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #12 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 173.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #13 is crystalline tabernanthalog monofumarate salt Pattern #13characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, and 16.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #13 is crystallinetabernanthalog monofumarate salt Pattern #13 characterized by XRPDsignals at 25.6°2θ, 16.0°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #13 is crystalline tabernanthalog monofumarate salt Pattern #13characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ, and19.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#13 is crystalline tabernanthalog monofumarate salt Pattern #13characterized by XRPD signals at of 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ,and 19.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #13 is crystalline tabernanthalog monofumarate salt Pattern #13characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ,19.7°2θ, 17.5°2θ, and 8.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #13 is crystalline tabernanthalog monofumaratesalt Pattern #13 characterized by XRPD signals at 25.6°2θ, 16.0°2θ,16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ, and 8.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #13 is crystalline tabernanthalog monofumarate salt Pattern #13characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ,19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ;or 0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #13 is crystallinetabernanthalog monofumarate salt Pattern #13 characterized by XRPDsignals at 25.6°2θ, 16.0°2θ, 16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ, 8.1°2θ,21.9°2θ, 9.1°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #13 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 174.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #15 is crystalline tabernanthalog monofumarate salt Pattern #15characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.2°2θ, 17.0°2θ, and 25.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #15 is crystallinetabernanthalog monofumarate salt Pattern #15 characterized by XRPDsignals 16.2°2θ, 17.0°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #15 is crystalline tabernanthalog monofumarate salt Pattern #15characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.2°2θ, 17.0°2θ, 25.5°2θ, 23.3°2θ, and21.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#15 is crystalline tabernanthalog monofumarate salt Pattern #15characterized by XRPD signals at of 16.2°2θ, 17.0°2θ, 25.5°2θ, 23.3°2θ,and 21.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #15 is crystalline tabernanthalog monofumarate salt Pattern #15characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.2°2θ, 17.0°2θ, 25.5°2θ, 23.3°2θ,21.0°2θ, 16.9°2θ, and 19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #15 is crystalline tabernanthalog monofumaratesalt Pattern #15 characterized by XRPD signals at 16.2°2θ, 17.0°2θ,25.5°2θ, 23.3°2θ, 21.0°2θ, 16.9°2θ, and 19.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #15 is crystalline tabernanthalog monofumarate salt Pattern #15characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 16.2°2θ, 17.0°2θ, 25.5°2θ, 23.3°2θ,21.0°2θ, 16.9°2θ, 19.9°2θ, 24.4°2θ, 8.4°2θ, and 25.1°2θ(±0.2°2θ;±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #15 is crystallinetabernanthalog monofumarate salt Pattern #15 characterized by XRPDsignals at 16.2°2θ, 17.0°2θ, 25.5°2θ, 23.3°2θ, 21.0°2θ, 16.9°2θ,19.9°2θ, 24.4°2θ, 8.4°2θ, and 25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #15 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 176.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #16 is crystalline tabernanthalog monofumarate salt Pattern #16characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #16 is crystallinetabernanthalog monofumarate salt Pattern #16 characterized by XRPDsignals 25.6°2θ, 16.4°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #16 is crystalline tabernanthalog monofumarate salt Pattern #16characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 17.0°2θ, 24.4°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#16 is crystalline tabernanthalog monofumarate salt Pattern #16characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 17.0°2θ, 24.4°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #16 is crystalline tabernanthalog monofumarate salt Pattern #16characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 17.0°2θ, 24.4°2θ,19.3°2θ, 9.1°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #16 is crystalline tabernanthalog monofumaratesalt Pattern #16 characterized by XRPD signals at 25.6°2θ, 16.4°2θ,17.0°2θ, 24.4°2θ, 19.3°2θ, 9.1°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #16 is crystalline tabernanthalog monofumarate salt Pattern #16characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 17.0°2θ, 24.4°2θ,19.3°2θ, 9.1°2θ, 16.8°2θ, 9.6°2θ, 18.1°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ;or 0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate salt Pattern #16 is crystallinetabernanthalog monofumarate salt Pattern #16 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, 17.0°2θ, 24.4°2θ, 19.3°2θ, 9.1°2θ, 16.8°2θ,9.6°2θ, 18.1°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #16 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 177.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #17 is crystalline tabernanthalog monofumarate salt Pattern #17characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, and 16.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #17 is crystallinetabernanthalog monofumarate salt Pattern #17 characterized by XRPDsignals 25.6°2θ, 16.4°2θ, and 16.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #17 is crystalline tabernanthalog monofumarate salt Pattern #17characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 16.6°2θ, 23.6°2θ, and21.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#17 is crystalline tabernanthalog monofumarate salt Pattern #17characterized by XRPD signals at 25.6°2θ, 16.4°2θ, 16.6°2θ, 23.6°2θ, and21.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #17 is crystalline tabernanthalog monofumarate salt Pattern #17characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 16.6°2θ, 23.6°2θ,21.7°2θ, 19.6°2θ, and 26.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #17 is crystalline tabernanthalog monofumaratesalt Pattern #17 characterized by XRPD signals at 25.6°2θ, 16.4°2θ,16.6°2θ, 23.6°2θ, 21.7°2θ, 19.6°2θ, and 26.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #17 is crystalline tabernanthalog monofumarate salt Pattern #17characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.4°2θ, 16.6°2θ, 23.6°2θ,21.7°2θ, 19.6°2θ, 26.9°2θ, 9.1°2θ, 22.4°2θ, and 23.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #17 is crystallinetabernanthalog monofumarate salt Pattern #17 characterized by XRPDsignals at 25.6°2θ, 16.4°2θ, 16.6°2θ, 23.6°2θ, 21.7°2θ, 19.6°2θ,26.9°2θ, 9.1°2θ, 22.4°2θ, and 23.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #17 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 178.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #18 is crystalline tabernanthalog monofumarate salt Pattern #18characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, and 18.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #18 is crystallinetabernanthalog monofumarate salt Pattern #18 characterized by XRPDsignals 25.6°2θ, 16.0°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #18 is crystalline tabernanthalog monofumarate salt Pattern #18characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#18 is crystalline tabernanthalog monofumarate salt Pattern #18characterized by XRPD signals at 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #18 is crystalline tabernanthalog monofumarate salt Pattern #18characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ,21.4°2θ, 26.8°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #18 is crystalline tabernanthalog monofumaratesalt Pattern #18 characterized by XRPD signals at 25.6°2θ, 16.0°2θ,18.0°2θ, 16.3°2θ, 21.4°2θ, 26.8°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #18 is crystalline tabernanthalog monofumarate salt Pattern #18characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ,21.4°2θ, 26.8°2θ, 23.0°2θ, 25.9°2θ, 15.5°2θ, and 11.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #18 is crystallinetabernanthalog monofumarate salt Pattern #18 characterized by XRPDsignals at 25.6°2θ, 16.0°2θ, 18.0°2θ, 16.3°2θ, 21.4°2θ, 26.8°2θ,23.0°2θ, 25.9°2θ, 15.5°2θ, and 11.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #18 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 179.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #19 is crystalline tabernanthalog monofumarate salt Pattern #19characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 25.5°2θ, and 16.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #19 is crystallinetabernanthalog monofumarate salt Pattern #19 characterized by XRPDsignals 25.6°2θ, 25.5°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #19 is crystalline tabernanthalog monofumarate salt Pattern #19characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 25.6°2θ, 25.5°2θ, 16.4°2θ, 20.5°2θ, and16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#19 is crystalline tabernanthalog monofumarate salt Pattern #19characterized by XRPD signals at 25.6°2θ, 25.5°2θ, 16.4°2θ, 20.5°2θ, and16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #19 is crystalline tabernanthalog monofumarate salt Pattern #19characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 25.5°2θ, 16.4°2θ, 20.5°2θ,16.3°2θ, 26.7°2θ, and 22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate salt Pattern #19 is crystalline tabernanthalog monofumaratesalt Pattern #19 characterized by XRPD signals at 25.6°2θ, 25.5°2θ,16.4°2θ, 20.5°2θ, 16.3°2θ, 26.7°2θ, and 22.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #19 is crystalline tabernanthalog monofumarate salt Pattern #19characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 25.6°2θ, 25.5°2θ, 16.4°2θ, 20.5°2θ,16.3°2θ, 26.7°2θ, 22.8°2θ, 19.5°2θ, 19.4°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #19 is crystallinetabernanthalog monofumarate salt Pattern #19 characterized by XRPDsignals at 25.6°2θ, 25.5°2θ, 16.4°2θ, 20.5°2θ, 16.3°2θ, 26.7°2θ,22.8°2θ, 19.5°2θ, 19.4°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #19 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 180.

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #20 is crystalline tabernanthalog monofumarate salt Pattern #20characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 6.1°2θ, 25.5°2θ, and 16.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog monofumarate salt Pattern #20 is crystallinetabernanthalog monofumarate salt Pattern #20 characterized by XRPDsignals 6.1°2θ, 25.5°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #20 is crystalline tabernanthalog monofumarate salt Pattern #20characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 6.1°2θ, 25.5°2θ, 16.3°2θ, 19.0°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate salt Pattern#20 is crystalline tabernanthalog monofumarate salt Pattern #20characterized by XRPD signals at 6.1°2θ, 25.5°2θ, 16.3°2θ, 19.0°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate saltPattern #20 is crystalline tabernanthalog monofumarate salt Pattern #20characterized by two or more, or three or more XRPD signals selectedfrom the group consisting 6.1°2θ, 25.5°2θ, 16.3°2θ, 19.0°2θ, 18.2°2θ,15.9°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog monofumarate saltPattern #20 is crystalline tabernanthalog monofumarate salt Pattern #20characterized by XRPD signals at 6.1°2θ, 25.5°2θ, 16.3°2θ, 19.0°2θ,18.2°2θ, 15.9°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog monofumarate saltPattern #20 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 181.

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #5 is crystalline tabernanthalog hemifumarate salt Pattern #5characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 16.9°2θ, and 21.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate salt Pattern #5 is crystallinetabernanthalog hemifumarate salt Pattern #5 characterized by XRPDsignals at 8.2°2θ, 16.9°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #5 is crystalline tabernanthalog hemifumarate salt Pattern #5characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 16.9°2θ, 21.4°2θ, 23.6°2θ, and20.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog hemifumarate salt Pattern#5 is crystalline tabernanthalog hemifumarate salt Pattern #5characterized by XRPD signals at 8.2°2θ, 16.9°2θ, 21.4°2θ, 23.6°2θ, and20.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #5 is crystalline tabernanthalog hemifumarate salt Pattern #5characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 16.9°2θ, 21.4°2θ, 23.6°2θ, 20.0°2θ, 11.1°2θ, and 15.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthaloghemifumarate salt Pattern #5 is crystalline tabernanthalog hemifumaratesalt Pattern #5 characterized by XRPD signals at 8.2°2θ, 16.9°2θ,21.4°2θ, 23.6°2θ, 20.0°2θ, 11.1°2θ, and 15.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #5 is crystalline tabernanthalog hemifumarate salt Pattern #5characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 16.9°2θ, 21.4°2θ, 23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ, 25.5°2θ, 22.5°2θ, and 23.9°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog hemifumarate salt Pattern #5 is crystallinetabernanthalog hemifumarate salt Pattern #5 characterized by XRPDsignals at 8.2°2θ, 16.9°2θ, 21.4°2θ, 23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ,25.5°2θ, 22.5°2θ, and 23.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate saltPattern #5 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 181B.

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 15.5°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate salt Pattern #14 is crystallinetabernanthalog hemifumarate salt Pattern #14 characterized by XRPDsignals at 8.2°2θ, 15.5°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, and20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog hemifumarate salt Pattern#14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by XRPD signals at 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, and20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, 20.2°2θ,11.2°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by XRPD signals at 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ,20.2°2θ, 11.2°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, 20.2°2θ,11.2°2θ, 23.7°2θ, 24.8°2θ, 21.5°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog hemifumarate salt Pattern #14 is crystallinetabernanthalog hemifumarate salt Pattern #14 characterized by XRPDsignals at 8.2°2θ, 15.5°2θ, 17.0°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ,24.8°2θ, 21.5°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate saltPattern #14 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 181D.

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 11.3°2θ, and 17.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate salt Pattern #14 is crystallinetabernanthalog hemifumarate salt Pattern #14 characterized by XRPDsignals at 8.2°2θ, 11.3°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 11.3°2θ, 17.1°2θ, 21.5°2θ, and20.3°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog hemifumarate salt Pattern#14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by XRPD signals at 8.2°2θ, 11.3°2θ, 17.1°2θ, 21.5°2θ, and20.3°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 11.3°2θ, 17.1°2θ, 21.5°2θ, 20.3°2θ,15.6°2θ, and 12.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by XRPD signals at 8.2°2θ, 11.3°2θ, 17.1°2θ, 21.5°2θ,20.3°2θ, 15.6°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #14 is crystalline tabernanthalog hemifumarate salt Pattern #14characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°2θ, 11.3°2θ, 17.1°2θ, 21.5°2θ, 20.3°2θ,15.6°2θ, 12.9°2θ, 19.1°2θ, 21.2°2θ, and 22.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog hemifumarate salt Pattern #14 is crystallinetabernanthalog hemifumarate salt Pattern #14 characterized by XRPDsignals at 8.2°2θ, 11.3°2θ, 17.1°2θ, 21.5°2θ, 20.3°2θ, 15.6°2θ, 12.9°2θ,19.1°2θ, 21.2°2θ, and 22.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate saltPattern #14 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 181E.

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #21 is crystalline tabernanthalog hemifumarate salt Pattern #21characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.2°2θ, 16.7°2θ, and 25.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate salt Pattern #21 is crystallinetabernanthalog hemifumarate salt Pattern #21 characterized by XRPDsignals at 19.2°2θ, 16.7°2θ, and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #21 is crystalline tabernanthalog hemifumarate salt Pattern #21characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.2°2θ, 16.7°2θ, 25.4°2θ, 22.2°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog hemifumarate salt Pattern#21 is crystalline tabernanthalog hemifumarate salt Pattern #21characterized by XRPD signals at 19.2°2θ, 16.7°2θ, 25.4°2θ, 22.2°2θ, and27.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #21 is crystalline tabernanthalog hemifumarate salt Pattern #21characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.2°2θ, 16.7°2θ, 25.4°2θ, 22.2°2θ,27.2°2θ, 18.1°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthaloghemifumarate salt Pattern #21 is crystalline tabernanthalog hemifumaratesalt Pattern #21 characterized by XRPD signals at 19.2°2θ, 16.7°2θ,25.4°2θ, 22.2°2θ, 27.2°2θ, 18.1°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #21 is crystalline tabernanthalog hemifumarate salt Pattern #21characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 19.2°2θ, 16.7°2θ, 25.4°2θ, 22.2°2θ,27.2°2θ, 18.1°2θ, 17.7°2θ, 21.2°2θ, 26.1°2θ, and 6.7°2θ(±0.2°2θ;±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate salt Pattern #21 is crystallinetabernanthalog hemifumarate salt Pattern #21 characterized by XRPDsignals at 19.2°2θ, 16.7°2θ, 25.4°2θ, 22.2°2θ, 27.2°2θ, 18.1°2θ,17.7°2θ, 21.2°2θ, 26.1°2θ, and 6.7°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate saltPattern #21 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 182.

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #22 is crystalline tabernanthalog hemifumarate salt Pattern #22characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 18.9°2θ, 19.3°2θ, and 16.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate salt Pattern #22 is crystallinetabernanthalog hemifumarate salt Pattern #22 characterized by XRPDsignals at 18.9°2θ, 19.3°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #22 is crystalline tabernanthalog hemifumarate salt Pattern #22characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 18.9°2θ, 19.3°2θ, 16.7°2θ, 27.3°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog hemifumarate salt Pattern#22 is crystalline tabernanthalog hemifumarate salt Pattern #22characterized by XRPD signals at 18.9°2θ, 19.3°2θ, 16.7°2θ, 27.3°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #22 is crystalline tabernanthalog hemifumarate salt Pattern #22characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 18.9°2θ, 19.3°2θ, 16.7°2θ, 27.3°2θ,18.2°2θ, 6.7°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthaloghemifumarate salt Pattern #22 is crystalline tabernanthalog hemifumaratesalt Pattern #22 characterized by XRPD signals at 18.9°2θ, 19.3°2θ,16.7°2θ, 27.3°2θ, 18.2°2θ, 6.7°2θ, and 25.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog hemifumarate saltPattern #22 is crystalline tabernanthalog hemifumarate salt Pattern #22characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 18.9°2θ, 19.3°2θ, 16.7°2θ, 27.3°2θ,18.2°2θ, 6.7°2θ, 25.5°2θ, 17.7°2θ, 20.2°2θ, and 22.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog hemifumarate salt Pattern #22 is crystallinetabernanthalog hemifumarate salt Pattern #22 characterized by XRPDsignals at 18.9°2θ, 19.3°2θ, 16.7°2θ, 27.3°2θ, 18.2°2θ, 6.7°2θ, 25.5°2θ,17.7°2θ, 20.2°2θ, and 22.3°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog hemifumarate saltPattern #22 is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven,twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three,thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight,thirty-nine, forty, forty-one, forty-two, forty-three, forty-four,forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty,fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six,fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two,sixty-three, sixty-four, sixty-five, or sixty-six XRPD signals selectedfrom those set forth in Table 183.

In some embodiments, the solid form of tabernanthalog monofumarate (FormA) is crystalline tabernanthalog monofumarate (Form A) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 16.2°2θ, 18.9°2θ, and 24.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate (FormA) is crystalline tabernanthalog monofumarate (Form A) characterized byXRPD signals at 16.2°2θ, 18.9°2θ, and 24.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate (FormA) is crystalline tabernanthalog monofumarate (Form A) characterized byXRPD signals at 16.2°2θ, 18.9°2θ, 19.2°2θ, 20.2°2θ, and 24.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate (FormA) is crystalline tabernanthalog monofumarate (Form A) characterized byXRPD signals at 16.2°2θ, 18.9°2θ, 19.2°2θ, 20.2°2θ, 21.6°2θ, 24.9°2θ,and 25.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate (FormA) is crystalline tabernanthalog monofumarate (Form A) characterized byXRPD signals at 15.7°2θ, 16.2°2θ, 18.9°2θ, 19.2°2θ, 20.2°2θ, 21.6°2θ,24.9°2θ, 25.8°2θ, 27.8°2θ, and 37.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten XRPD signals selected from those set forth in Table 258.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.4°2θ, 26.0°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate characterized byXRPD signals at 19.4°2θ, 26.0°2θ, and 17.0°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.4°2θ, 26.0°2θ, 17.0°2θ, 12.9°2θ, and 24.5°2θ (±0.2°2θ;±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratecharacterized by XRPD signals at 19.4°2θ, 26.0°2θ, 17.0°2θ, 12.9°2θ, and24.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.4°2θ, 26.0°2θ, 17.0°2θ, 12.9°2θ, 24.5°2θ, 20.6°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by XRPD signals at19.4°2θ, 26.0°2θ, 17.0°2θ, 12.9°2θ, 24.5°2θ, 20.6°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of15.6°2θ, 19.4°2θ, 26.0°2θ, 17.0°2θ, 12.9°2θ, 24.5°2θ, 20.6°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by XRPD signals at15.6°2θ, 19.4°2θ, 26.0°2θ, 17.0°2θ, 12.9°2θ, 24.5°2θ, 20.6°2θ, and18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, or eight XRPDsignals selected from those set forth in Table 321.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 18.1°2θ, 27.2°2θ, 26.8°2θ, 9°2θ, 22.3°2θ, 25.1°2θ, 26.1°2θ,17.4°2θ, 23.1°2θ, 14.2°2θ, 30° θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 27.2 °2θ, 26.8°2θ, 9°2θ, 22.3°2θ,25.1°2θ, 26.1°2θ, 17.4°2θ, 23.1°2θ, 14.2°2θ, 30°2θ, and 17.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals as shown in Table 155.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 18.1°2θ, 26.8°2θ, 9°2θ, 22.3°2θ, 27.2°2θ, 24.6°2θ, 17.4°2θ,17.8°2θ, 15.6°2θ, 23.1°2θ, 25.1°2θ, 26.2°2θ, and 18.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, and19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 18.1°2θ, 26.8°2θ, 9°2θ, 22.3°2θ, 27.2°2θ,24.6°2θ, 17.4°2θ, 17.8°2θ, 15.6°2θ, 23.1°2θ, 25.1°2θ, 26.2°2θ, and18.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals as shown in Table 156.

In some embodiments, the tabernanthalog fumarate salt has an ¹H NMRspectra as provided in FIGS. 295 and 296 .

In some embodiments, the tabernanthalog fumarate salt has a TGA profileas provided in FIG. 299 .

In some embodiments, the TGA profile of the tabernanthalog fumarate saltshows a first TG event (−2.1% w/w).

In some embodiments, the tabernanthalog fumarate salt has a DSC profileas provided in FIG. 300 .

In some embodiments, the DSC profile of the tabernanthalog fumarate saltexhibits a bimodal transition corresponding to the melting of twodifferent crystal forms.

In some embodiments, the tabernanthalog fumarate salt has a DVS profileas provided in FIG. 301 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 5.1°2θ, 10.2°2θ, 27.2°2θ, 18.1°2θ, 9°2θ, 26.8°2θ, 22.3°2θ,25.2°2θ, 17.4°2θ, 26.1°2θ, 17.7°2θ, 23°2θ, 29.9°2θ, and 6.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 5.1°2θ, 10.2°2θ, 27.2°2θ, 18.1°2θ, 9°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 5.1°2θ, 10.2°2θ, 27.2°2θ, 18.1°2θ, 9°2θ,26.8°2θ, 22.3°2θ, 25.2°2θ, 17.4°2θ, 26.1°2θ, 17.7°2θ, 23°2θ, 29.9°2θ,and 6.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 5.1°2θ, 10.2°2θ, 27.2°2θ, 18.1°2θ, 9°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #1 characterized by two or more, or three XRPDsignals as shown in Table 157.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, 17.1°2θ,23°2θ, 9.1°2θ, 27.3°2θ, 15.7°2θ, 26.8°2θ, 18.1°2θ, 20.7°2θ, 12.3°2θ,25°2θ, 22.8°2θ, 21°2θ, 14.2°2θ, 24.7°2θ, 17.4°2θ, 18.8°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by XRPD signals at 25.6°2θ,16.4°2θ, 17.1°2θ, 23°2θ, 9.1°2θ, 27.3°2θ, 15.7°2θ, 26.8°2θ, 18.1°2θ,20.7°2θ, 12.3°2θ, 25°2θ, 22.8°2θ, 21°2θ, 14.2°2θ, 24.7°2θ, 17.4°2θ,18.8°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by XRPD signals at 25.6°2θ,16.4°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by two or more, or three XRPDsignals as shown in Table 158.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by an ¹H NMR spectrum as depictedin FIG. 313 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by an XRPD profile as depicted inFIG. 3 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by a TGA profile as depicted inFIG. 315 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2a characterized by a DSC profile as depicted inFIG. 316 . In some embodiments, the tabernanthalog monofumarate salt iscrystalline polymorphic Pattern #2b characterized by two or more, orthree XRPD signals selected from the group consisting of 25.5°2θ,16.3°2θ, 24.6°2θ, 18.1°2θ, 9°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ,17°2θ, 22.6°2θ, 17.4°2θ, 19.4°2θ, 22.3°2θ, 14.2°2θ, 18.8°2θ, and21°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2b characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 24.6°2θ,18.1°2θ, 9°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ, and 17°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2b characterized by XRPD signals at 25.5°2θ,16.3°2θ, 24.6°2θ, 18.1°2θ, 9°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ,17°2θ, 22.6°2θ, 17.4°2θ, 19.4°2θ, 22.3°2θ, 14.2°2θ, 18.8°2θ, and21°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2b characterized by XRPD signals at 25.5°2θ,16.3°2θ, 24.6°2θ, 18.1°2θ, 9°2θ, 25.1°2θ, 15.8°2θ, 26.8°2θ, 15.5°2θ, and17°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2b characterized by two or more, or three XRPDsignals as shown in Table 159.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 22.3°2θ, 27.2°2θ, 9°2θ, 18.1°2θ, 26.8°2θ, 17.7°2θ, 26.1°2θ,23°2θ, 25.1°2θ, 17.4°2θ, 21.2°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 19.3°2θ,16.7°2θ, 22.3°2θ, 27.2°2θ, 9°2θ, 18.1°2θ, 26.8°2θ, and 17.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 27.2°2θ, 9°2θ, 18.1°2θ, 26.8°2θ,17.7°2θ, 26.1°2θ, 23°2θ, 25.1°2θ, 17.4°2θ, 21.2°2θ, and 20.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by XRPD signals at 25.5°2θ,16.3°2θ, 19.3°2θ, 16.7°2θ, 22.3°2θ, 27.2°2θ, 9°2θ, 18.1°2θ, 26.8°2θ, and17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2c characterized by two or more, or three XRPDsignals as shown in Table 160.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.3°2θ, 16.2°2θ,25.2°2θ, 9.1°2θ, 22.1°2θ, 26°2θ, 26.8°2θ, 18.1°2θ, 19.9°2θ, 21.1°2θ,17.5°2θ, 14.2°2θ, 30°2θ, 27.2° 20, and 28.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.3°2θ, 16.2°2θ,25.2°2θ, 9.1°2θ, 22.1°2θ, 26°2θ, 26.8°2θ, 18.1°2θ, and 19.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by XRPD signals at 25.6°2θ,16.3°2θ, 16.2°2θ, 25.2°2θ, 9.1°2θ, 22.1°2θ, 26°2θ, 26.8°2θ, 18.1°2θ,19.9°2θ, 21.1°2θ, 17.5°2θ, 14.2°2θ, 30°2θ, 27.2°2θ, and 28.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by XRPD signals at 25.6°2θ,16.3°2θ, 16.2°2θ, 25.2°2θ, 9.1°2θ, 22.1°2θ, 26°2θ, 26.8°2θ, 18.1°2θ, and19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #2d characterized by two or more, or three XRPDsignals as shown in Table 161.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 16.6°2θ,20.1°2θ, 26.0°2θ, 22.2°2θ, 26.8°2θ, 16.8°2θ, 18.8°2θ, 9.0°2θ, 22.5°2θ,18°2θ, 25°2θ, 11.1°2θ, 24.7°2θ, 12.5°2θ, 14.4°2θ, 14.3°2θ, 8.4°2θ,19.3°2θ, 27.2°2θ, 17.4°2θ, 29.9°2θ, and 9.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 16.6°2θ,20.1°2θ, 26.0°2θ, 22.2°2θ, 26.8°2θ, 16.8°2θ, 18.8°2θ, and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 16.6°2θ, 20.1°2θ, 26.0°2θ, 22.2°2θ, 26.8°2θ, 16.8°2θ, 18.8°2θ,9.0°2θ, 22.5°2θ, 18°2θ, 25°2θ, 11.1°2θ, 24.7°2θ, 12.5°2θ, 14.4°2θ,14.3°2θ, 8.4°2θ, 19.3°2θ, 27.2°2θ, 17.4°2θ, 29.9°2θ, and 9.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 16.6°2θ, 20.1°2θ, 26.0°2θ, 22.2°2θ, 26.8°2θ, 16.8°2θ, 18.8°2θ,and 9.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #3 characterized by two or more, or three XRPDsignals as shown in Table 162.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 8.2°2θ,11.3°2θ, 9.0°2θ, 23.8°2θ, 19.3°2θ, 17.1°2θ, 19.4°2θ, 26.8°2θ, 21.5°2θ,18°2θ, 20.5°2θ, 20.4°2θ, 15.6°2θ, 25.2°2θ, 22.6°2θ, 18.9°2θ, 14.2°2θ,12.7°2θ, and 30°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 8.2°2θ,11.3°2θ, 9.0°2θ, 23.8°2θ, 19.3°2θ, 17.1°2θ, 19.4°2θ, and26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by XRPD signals at 25.5°2θ,16.3°2θ, 8.2°2θ, 11.3°2θ, 9.0°2θ, 23.8°2θ, 19.3°2θ, 17.1°2θ, 19.4°2θ,26.8°2θ, 21.5°2θ, 18°2θ, 20.5°2θ, 20.4°2θ, 15.6°2θ, 25.2°2θ, 22.6°2θ,18.9°2θ, 14.2°2θ, 12.7°2θ, and 30°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by XRPD signals at 25.5°2θ,16.3°2θ, 8.2°2θ, 11.3°2θ, 9.0°2θ, 23.8°2θ, 19.3°2θ, 17.1°2θ, 19.4°2θ,and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4a characterized by two or more, or three XRPDsignals as shown in Table 163.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.3°2θ, 8.2°2θ,9.1°2θ, 17.2°2θ, 18.1°2θ, 26.8°2θ, 15.7°2θ, 27.3°2θ, 21.5°2θ, 11.3°2θ,22.6°2θ, 23.9°2θ, 25.2°2θ, 20.4°2θ, 21.4°2θ, 19.3°2θ, 17.4°2θ, 14.2°2θ,16.8°2θ, 18.8°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.3°2θ, 8.2°2θ,9.1°2θ, 17.2°2θ, 18.1°2θ, 26.8°2θ, 15.7°2θ, 27.3°2θ, and21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by XRPD signals at 25.6°2θ,16.3°2θ, 8.2°2θ, 9.1°2θ, 17.2°2θ, 18.1°2θ, 26.8°2θ, 15.7°2θ, 27.3°2θ,21.5°2θ, 11.3°2θ, 22.6°2θ, 23.9°2θ, 25.2°2θ, 20.4°2θ, 21.4°2θ, 19.3°2θ,17.4°2θ, 14.2°2θ, 16.8°2θ, 18.8°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by XRPD signals at 25.6°2θ,16.3°2θ, 8.2°2θ, 9.1°2θ, 17.2°2θ, 18.1°2θ, 26.8°2θ, 15.7°2θ, 27.3°2θ,and 21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #4b characterized by two or more, or three XRPDsignals as shown in Table 164.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 16.9°2θ, 21.4°2θ,23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ, 25.5°2θ, 22.5°2θ, 23.9°2θ, 30.2°2θ,22.2°2θ, 19.1°2θ, 16.3°2θ, 12.8°2θ, and 26.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 16.9°2θ, 21.4°2θ,23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ, 25.5°2θ, 22.5°2θ, and23.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by XRPD signals at 8.2°2θ, 16.9°2θ,21.4°2θ, 23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ, 25.5°2θ, 22.5°2θ, 23.9°2θ,30.2°2θ, 22.2°2θ, 19.1°2θ, 16.3°2θ, 12.8°2θ, and 26.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by XRPD signals at 8.2°2θ, 16.9°2θ,21.4°2θ, 23.6°2θ, 20.0°2θ, 11.1°2θ, 15.4°2θ, 25.5°2θ, 22.5°2θ, and23.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #5 characterized by two or more, or three XRPDsignals as shown in Table 181B.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, 26.2°2θ, 22.1°2θ, 33.6°2θ, and 13°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, 26.2°2θ, 22.1°2θ, and 33.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, 26.2°2θ, and 22.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, 19.3°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,25.4°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, 20.7°2θ,and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals selected from the group consisting of 19.6°2θ, 16.6°2θ, and20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, 25.4°2θ, 19.3°2θ, 26.2°2θ, 22.1°2θ, 33.6°2θ, and13°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, 25.4°2θ, 19.3°2θ, 26.2°2θ, 22.1°2θ, and33.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, 25.4°2θ, 19.3°2θ, 26.2°2θ, and 22.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, 25.4°2θ, 19.3°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, 25.4°2θ, and 19.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, 20.7°2θ, and 25.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by XRPD signals at 19.6°2θ,16.6°2θ, and 20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by two or more, or three XRPDsignals as shown in Table 166.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by an ¹H NMR spectrum as depictsin FIG. 344 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by an XRPD profile as depicts inFIG. 13 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by TGA profile as depicted in FIG.347 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6a characterized by a DSC profile as depicted inFIG. 348 .

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6b characterized by two or more, or three XRPDsignals selected from the group consisting of 19.4°2θ, 16.5°2θ, 20.5°2θ,25.3°2θ, 26°2θ, 22°2θ, 12.9°2θ, 8.2°2θ, 33.4°2θ, and 37.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6b characterized by XRPD signals at 19.4°2θ,16.5°2θ, 20.5°2θ, 25.3°2θ, 26°2θ, 22°2θ, 12.9°2θ, 8.2°2θ, 33.4°2θ, and37.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #6b characterized by two or more, or three XRPDsignals as shown in Table 167.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.4°2θ, 25.6°2θ, 15.9°2θ,7.2°2θ, 24.9°2θ, 19.4°2θ, 9.1°2θ, 21.3°2θ, 19.8°2θ, 16.8°2θ, 27.3°2θ,22.5°2θ, 18.2°2θ, 26.9°2θ, 14.3°2θ, 20.8°2θ, and 17.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.4°2θ, 25.6°2θ, 15.9°2θ,7.2°2θ, 24.9°2θ, 19.4°2θ, 9.1°2θ, 21.3°2θ, 19.8°2θ, and 16.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by XRPD signals at 16.4°2θ,25.6°2θ, 15.9°2θ, 7.2°2θ, 24.9°2θ, 19.4°2θ, 9.1°2θ, 21.3°2θ, 19.8°2θ,16.8°2θ, 27.3°2θ, 22.5°2θ, 18.2°2θ, 26.9°2θ, 14.3°2θ, 20.8°2θ, and17.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by XRPD signals at 16.4°2θ,25.6°2θ, 15.9°2θ, 7.2°2θ, 24.9°2θ, 19.4°2θ, 9.1°2θ, 21.3°2θ, 19.8°2θ,and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #7 characterized by two or more, or three XRPDsignals as shown in Table 168.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #8 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 15.8°2θ,24.2°2θ, 20.5°2θ, 24.8°2θ, 18°2θ, 19°2θ, 7.6°2θ, 9°2θ, 26.7°2θ, 22.5°2θ,27.2°2θ, 17.4°2θ, 18.9°2θ, 19.5°2θ, 22.3°2θ, 21.9°2θ, and14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #8 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.3°2θ, 15.8°2θ,24.2°2θ, 20.5°2θ, 24.8°2θ, 18°2θ, 19°2θ, 7.6°2θ, and 9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #8 characterized by XRPD signals at 25.5°2θ,16.3°2θ, 15.8°2θ, 24.2°2θ, 20.5°2θ, 24.8°2θ, 18°2θ, 19°2θ, 7.6°2θ, 9°2θ,26.7°2θ, 22.5°2θ, 27.2°2θ, 17.4°2θ, 18.9°2θ, 19.5°2θ, 22.3°2θ, 21.9°2θ,and 14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumaratefmonoumarate salt iscrystalline polymorphic Pattern #8 characterized by XRPD signals at25.5°2θ, 16.3°2θ, 15.8°2θ, 24.2°2θ, 20.5°2θ, 24.8°2θ, 18°2θ, 19°2θ,7.6°2θ, and 9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #8 characterized by two or more, or three XRPDsignals as shown in Table 169.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by two or more, or three XRPDsignals selected from the group consisting of 15.9°2θ, 25.6°2θ, 24.7°2θ,16.4°2θ, 19.5°2θ, 21.9°2θ, 17.1°2θ, 8°2θ, 9.2°2θ, 20.8°2θ, 27 °2θ,18.2°2θ, 28.8°2θ, 19.2°2θ, 22.4°2θ, 14.3°2θ, 10.5°2θ, 12.2°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by two or more, or three XRPDsignals selected from the group consisting of 15.9°2θ, 25.6°2θ, 24.7°2θ,16.4°2θ, 19.5°2θ, 21.9°2θ, 17.1°2θ, 8°2θ, 9.2°2θ, and 20.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by XRPD signals at 15.9°2θ,25.6°2θ, 24.7°2θ, 16.4°2θ, 19.5°2θ, 21.9°2θ, 17.1°2θ, 8°2θ, 9.2°2θ,20.8°2θ, 27°2θ, 18.2°2θ, 28.8°2θ, 19.2°2θ, 22.4°2θ, 14.3°2θ, 10.5°2θ,12.2°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by XRPD signals at 15.9°2θ,25.6°2θ, 24.7°2θ, 16.4°2θ, 19.5°2θ, 21.9°2θ, 17.1°2θ, 8°2θ, 9.2°2θ, and20.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #9 characterized by two or more, or three XRPDsignals as shown in Table 170.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #10 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.9°2θ, 16.3°2θ,21.3°2θ, 23.5°2θ, 8.2°2θ, 10.8°2θ, 23.4°2θ, 9.1°2θ, 19.8°2θ, 15.2°2θ,23.6°2θ, 26.8°2θ, 21.8°2θ, 22.2°2θ, 18°2θ, 25.2°2θ, 19.6°2θ, 14.2°2θ,19.1°2θ, 29.8°2θ, 22.6°2θ, 17.4°2θ, 26.1°2θ, and 18.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #10 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.5°2θ, 16.9°2θ, 16.3°2θ,21.3°2θ, 23.5°2θ, 8.2°2θ, 10.8°2θ, 23.4°2θ, 9.1°2θ, and 19.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #10 characterized by XRPD signals at 25.5°2θ,16.9°2θ, 16.3°2θ, 21.3°2θ, 23.5°2θ, 8.2°2θ, 10.8°2θ, 23.4°2θ, 9.1°2θ,19.8°2θ, 15.2°2θ, 23.6°2θ, 26.8°2θ, 21.8°2θ, 22.2°2θ, 18°2θ, 25.2°2θ,19.6°2θ, 14.2°2θ, 19.1°2θ, 29.8°2θ, 22.6°2θ, 17.4°2θ, 26.1°2θ, and18.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #10 characterized by XRPD signals at 25.5°2θ,16.9°2θ, 16.3°2θ, 21.3°2θ, 23.5°2θ, 8.2°2θ, 10.8°2θ, 23.4°2θ, 9.1°2θ,and 19.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #10 characterized by two or more, or three XRPDsignals as shown in Table 171.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.1°2θ, 25.7°2θ, 16.4°2θ,21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 20.9°2θ, 17.4°2θ, 22.8°2θ,11.2°2θ, 27°2θ, 24°2θ, 18.2°2θ, 10.8°2θ, 25.3°2θ, 22.5°2θ, and14.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.1°2θ, 25.7°2θ, 16.4°2θ,21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 20.9°2θ, and 17.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by XRPD signals at 16.1°2θ,25.7°2θ, 16.4°2θ, 21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 20.9°2θ,17.4°2θ, 22.8°2θ, 11.2°2θ, 27°2θ, 24°2θ, 18.2°2θ, 10.8°2θ, 25.3°2θ,22.5°2θ, and 14.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by XRPD signals at 16.1°2θ,25.7°2θ, 16.4°2θ, 21.6°2θ, 20.4°2θ, 7.5°2θ, 9.2°2θ, 23.9°2θ, 20.9°2θ,and 17.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #11 characterized by two or more, or three XRPDsignals as shown in Table 172.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #12 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.3°2θ, 25.6°2θ, 21.6°2θ,20.3°2θ, 8.3°2θ, 9.1°2θ, 18.2°2θ, 23°2θ, 10.8°2θ, and 14.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #12 characterized by XRPD signals at 16.3°2θ,25.6°2θ, 21.6°2θ, 20.3°2θ, 8.3°2θ, 9.1°2θ, 18.2°2θ, 23°2θ, 10.8°2θ, and14.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #12 characterized by two or more, or three XRPDsignals as shown in Table 173.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16°2θ, 16.4°2θ,25.0°2θ, 19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, 10.5°2θ, 26.9 °2θ,20.9°2θ, 18.1°2θ, 22.7°2θ, 23.4°2θ, 24.5°2θ, 28.7°2θ, 14.3°2θ, and18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16°2θ, 16.4°2θ,25.0°2θ, 19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, and 10.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by XRPD signals at 25.6°2θ, 16°2θ,16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, 10.5°2θ,26.9°2θ, 20.9°2θ, 18.1°2θ, 22.7°2θ, 23.4°2θ, 24.5°2θ, 28.7°2θ, 14.3°2θ,and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by XRPD signals at 25.6°2θ, 16°2θ,16.4°2θ, 25.0°2θ, 19.7°2θ, 17.5°2θ, 8.1°2θ, 21.9°2θ, 9.1°2θ, and10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #13 characterized by two or more, or three XRPDsignals as shown in Table 174.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, 24.8°2θ, 21.5°2θ, 18.1°2θ, 19.2°2θ,24.3°2θ, 19.4°2θ, 18.4°2θ, 21.3°2θ, and 12.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, 24.8°2θ, 21.5°2θ, and18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, 24.8°2θ, and 21.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, and 24.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,22.6°2θ, 20.2°2θ, 11.2°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,22.6°2θ, 20.2°2θ, and 11.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,22.6°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, 17°2θ,and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals selected from the group consisting of 8.2°2θ, 15.5°2θ, and17°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, 24.8°2θ, 21.5°2θ,18.1°2θ, 19.2°2θ, 24.3°2θ, 19.4°2θ, 18.4°2θ, 21.3°2θ, and12.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, 24.8°2θ, 21.5°2θ,and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, 24.8°2θ, and21.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, 23.7°2θ, and 24.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, 22.6°2θ, 20.2°2θ, 11.2°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, 22.6°2θ, 20.2°2θ, and 11.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, 22.6°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, 17°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by XRPD signals at 8.2°2θ,15.5°2θ, and 17°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by two or more, or three XRPDsignals as shown in Table 181D.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by an ¹H NMR spectrum as depictedin FIG. 377E.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by an XRPD profile as depicted inFIG. 377F.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by a TGA profile as depicted inFIG. 377I.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #14 characterized by a DSC profile as depicted inFIG. 377J.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.2°2θ, 17°2θ, 25.5°2θ,23.3°2θ, 21°2θ, 16.9°2θ, 19.9°2θ, 24.4°2θ, 8.4°2θ, 25.1°2θ, 18°2θ,15°2θ, 26°2θ, 17.7°2θ, 9°2θ, 10.5°2θ, 18.9°2θ, 23.6°2θ, 26.7°2θ,22.5°2θ, 24.8°2θ, and 19.2°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by two or more, or three XRPDsignals selected from the group consisting of 16.2°2θ, 17°2θ, 25.5°2θ,23.3°2θ, 21°2θ, 16.9°2θ, 19.9°2θ, 24.4°2θ, 8.4°2θ, and 25.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by XRPD signals at 16.2°2θ, 17°2θ,25.5°2θ, 23.3°2θ, 21°2θ, 16.9°2θ, 19.9°2θ, 24.4°2θ, 8.4°2θ, 25.1°2θ,18°2θ, 15°2θ, 26°2θ, 17.7°2θ, 9°2θ, 10.5°2θ, 18.9°2θ, 23.6°2θ, 26.7°2θ,22.5°2θ, 24.8°2θ, and 19.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by XRPD signals at 16.2°2θ, 17°2θ,25.5°2θ, 23.3°2θ, 21°2θ, 16.9°2θ, 19.9°2θ, 24.4°2θ, 8.4°2θ, and25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #15 characterized by two or more, or three XRPDsignals as shown in Table 176.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, 17°2θ,24.4°2θ, 19.3°2θ, 9.1°2θ, 16.8°2θ, 9.6°2θ, 18.1°2θ, 22.4°2θ, 17.8°2θ,27.3°2θ, 26.8°2θ, 20.3°2θ, 25.2°2θ, 19°2θ, 17.5°2θ, 9°2θ, 26.2°2θ,14.2°2θ, 23.8°2θ, and 23.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, 17°2θ,24.4°2θ, 19.3°2θ, 9.1°2θ, 16.8°2θ, 9.6°2θ, 18.1°2θ, and 22.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by XRPD signals at 25.6°2θ,16.4°2θ, 17°2θ, 24.4°2θ, 19.3°2θ, 9.1°2θ, 16.8°2θ, 9.6°2θ, 18.1°2θ,22.4°2θ, 17.8°2θ, 27.3°2θ, 26.8°2θ, 20.3°2θ, 25.2°2θ, 19°2θ, 17.5°2θ,9°2θ, 26.2°2θ, 14.2°2θ, 23.8°2θ, and 23.2°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by XRPD signals at 25.6°2θ,16.4°2θ, 17°2θ, 24.4°2θ, 19.3°2θ, 9.1°2θ, 16.8°2θ, 9.6°2θ, 18.1°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #16 characterized by two or more, or three XRPDsignals as shown in Table 177.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, 16.6°2θ,23.6°2θ, 21.7°2θ, 19.6°2θ, 26.9°2θ, 9.1°2θ, 22.4°2θ, 23.2°2θ, 18.1°2θ,27.1°2θ, 8.1°2θ, 11.2°2θ, 25.2°2θ, 15.4°2θ, 30.3°2θ, 14.3°2θ, and21.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16.4°2θ, 16.6°2θ,23.6°2θ, 21.7°2θ, 19.6°2θ, 26.9°2θ, 9.1°2θ, 22.4°2θ, and23.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by XRPD signals at 25.6°2θ,16.4°2θ, 16.6°2θ, 23.6°2θ, 21.7°2θ, 19.6°2θ, 26.9°2θ, 9.1°2θ, 22.4°2θ,23.2°2θ, 18.1°2θ, 27.1°2θ, 8.1°2θ, 11.2°2θ, 25.2°2θ, 15.4°2θ, 30.3°2θ,14.3°2θ, and 21.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by XRPD signals at 25.6°2θ,16.4°2θ, 16.6°2θ, 23.6°2θ, 21.7°2θ, 19.6°2θ, 26.9°2θ, 9.1°2θ, 22.4°2θ,and 23.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #17 characterized by two or more, or three XRPDsignals as shown in Table 178.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16°2θ, 18°2θ,16.3°2θ, 21.4°2θ, 26.8°2θ, 23°2θ, 25.9°2θ, 15.5°2θ, 11.0°2θ, 18.9°2θ,20.9°2θ, 22.4°2θ, 14.1°2θ, 19.3°2θ, 12.6°2θ, 16.8°2θ, 24.9°2θ, 9.1°2θ,12.1°2θ, and 8.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 16°2θ, 18°2θ,16.3°2θ, 21.4°2θ, 26.8°2θ, 23°2θ, 25.9°2θ, 15.5°2θ, and 11.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by XRPD signals at 25.6°2θ, 16°2θ,18°2θ, 16.3°2θ, 21.4°2θ, 26.8°2θ, 23°2θ, 25.9°2θ, 15.5°2θ, 11.0°2θ,18.9°2θ, 20.9°2θ, 22.4°2θ, 14.1°2θ, 19.3°2θ, 12.6°2θ, 16.8°2θ, 24.9°2θ,9.1°2θ, 12.1°2θ, and 8.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by XRPD signals at 25.6°2θ, 16°2θ,18°2θ, 16.3°2θ, 21.4°2θ, 26.8°2θ, 23°2θ, 25.9°2θ, 15.5°2θ, and11.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #18 characterized by two or more, or three XRPDsignals as shown in Table 179.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 25.5°2θ, 16.4°2θ,20.5°2θ, 16.3°2θ, 26.7°2θ, 22.8°2θ, 19.5°2θ, 19.4°2θ, 17.0°2θ, 33.3°2θ,9.1°2θ, 21.5°2θ, 27.1°2θ, 21.9°2θ, 24.7°2θ, 18.6°2θ, 15.7°2θ, 12.2°2θ,and 29.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by two or more, or three XRPDsignals selected from the group consisting of 25.6°2θ, 25.5°2θ, 16.4°2θ,20.5°2θ, 16.3°2θ, 26.7°2θ, 22.8°2θ, 19.5°2θ, 19.4°2θ, and 17°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by XRPD signals at 25.6°2θ,25.5°2θ, 16.4°2θ, 20.5°2θ, 16.3°2θ, 26.7°2θ, 22.8°2θ, 19.5°2θ, 19.4°2θ,17°2θ, 33.3°2θ, 9.1°2θ, 21.5°2θ, 27.1°2θ, 21.9°2θ, 24.7°2θ, 18.6°2θ,15.7°2θ, 12.2°2θ, and 29.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by XRPD signals at 25.6°2θ,25.5°2θ, 16.4°2θ, 20.5°2θ, 16.3°2θ, 26.7°2θ, 22.8°2θ, 19.5°2θ, 19.4°2θ,and 17°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #19 characterized by two or more, or three XRPDsignals as shown in Table 180.

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #20 characterized by two or more, or three XRPDsignals selected from the group consisting of 6.1°2θ, 25.5°2θ, 16.3°2θ,19°2θ, 18.2°2θ, 15.9°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #20 characterized by XRPD signals at 6.1°2θ,25.5°2θ, 16.3°2θ, 19°2θ, 18.2°2θ, 15.9°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog monofumarate salt is crystallinepolymorphic Pattern #20 characterized by two or more, or three XRPDsignals as shown in Table 181.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by two or more, or three XRPDsignals selected from the group consisting of 19.2°2θ, 16.7°2θ, 25.4°2θ,22.2°2θ, 27.2°2θ, 18.1°2θ, 17.7°2θ, 21.2°2θ, 26.1°2θ, 6.7°2θ, 20.1°2θ,17.6°2θ, 12.8°2θ, 23°2θ, 23.6°2θ, 28.7°2θ, 14.9°2θ, 30.1°2θ, 8.2°2θ, and16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by two or more, or three XRPDsignals selected from the group consisting of 19.2°2θ, 16.7°2θ, 25.4°2θ,22.2°2θ, 27.2°2θ, 18.1°2θ, 17.7°2θ, 21.2°2θ, 26.1°2θ, and6.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by XRPD signals at 19.2°2θ,16.7°2θ, 25.4°2θ, 22.2°2θ, 27.2°2θ, 18.1°2θ, 17.7°2θ, 21.2°2θ, 26.1°2θ,6.7°2θ, 20.1°2θ, 17.6°2θ, 12.8°2θ, 23°2θ, 23.6°2θ, 28.7°2θ, 14.9°2θ,30.1°2θ, 8.2°2θ, and 16.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by XRPD signals at 19.2°2θ,16.7°2θ, 25.4°2θ, 22.2°2θ, 27.2°2θ, 18.1°2θ, 17.7°2θ, 21.2°2θ, 26.1°2θ,and 6.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #21 characterized by two or more, or three XRPDsignals as shown in Table 182.

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by two or more, or three XRPDsignals selected from the group consisting of 18.9°2θ, 19.3°2θ, 16.7°2θ,27.3°2θ, 18.2°2θ, 25.5°2θ, 6.7°2θ, 17.7°2θ, 20.2°2θ, 22.3°2θ, 26.2°2θ,15.0°2θ, 23.7°2θ, 10.4°2θ, 21.3°2θ, 12.9°2θ, 25.4°2θ, and23.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by two or more, or three XRPDsignals selected from the group consisting of 18.9°2θ, 19.3°2θ, 16.7°2θ,27.3°2θ, 18.2°2θ, 25.5°2θ, 6.7°2θ, 17.7°2θ, 20.2°2θ, and22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by XRPD signals at 18.9°2θ,19.3°2θ, 16.7°2θ, 27.3°2θ, 18.2°2θ, 25.5°2θ, 6.7°2θ, 17.7°2θ, 20.2°2θ,22.3°2θ, 26.2°2θ, 15°2θ, 23.7°2θ, 10.4°2θ, 21.3°2θ, 12.9°2θ, 25.4°2θ,and 23.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by XRPD signals at 18.9°2θ,19.3°2θ, 16.7°2θ, 27.3°2θ, 18.2°2θ, 25.5°2θ, 6.7°2θ, 17.7°2θ, 20.2°2θ,and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog hemifumarate salt is crystallinepolymorphic Pattern #22 characterized by two or more, or three XRPDsignals as shown in Table 183.

In some embodiments, the tabernanthalog monofumarate salt has Pattern#6a (Form A) and is characterized by at least one of the followingproperties:

(a) 33.5% w/w th. of fumaric acid;

(b) a hydrogen bonding network wherein the fumaric acid adopted a1,4-orientated linear configuration, exhibiting head to tail hydrogenbonding between oxygen atoms O3----O4 (2.48 Å), while oxygen atom O2 washydrogen bonded to nitrogen atom N1, located on the azepine ring(O2----N1, 2.70 Å), assumed to be salified;

(c) monoclinic crystal system 300(2) with P2_(1/c) space group 300(2);

(d) a unit cell 300(2) K: a=7.43280(10)Å, b=8.59740(10)Å, c=27.5143(3)Å,a=g=90°, b=96.6990(10)°, V=1746.24(4) Å³;

(e) an asymmetric unit which contained one molecule of API and onemolecule of fumaric acid (crystal bonded);

(f) one or more, or two or more, or three or more XRPD signals selectedfrom the group consisting of 12.9°, 14.1°, 15.8°, 16.5°, 19.2°, 19.4°,20.6°, 22.0°, 25.2°, 26.0°, 28.0°, 33.4°,°(2θ, 1 d.p);

(g) a DSC profile exhibiting an onset at 187.0° C. (−117.9 Jg⁻¹,endotherm, melt) as shown in FIG. 149 ;

(h) a TGA profile exhibiting onsets at 220.8° C. (−16.0% w/w, ablation),289.5° C. (−1.2% w/w, ablation), 315.3° C. (−1.5% w/w, ablation), 325.9°C. (−3.8% w/w, ablation), 373.7° C. (−14.0% w/w, ablation) as shown inFIG. 148 ;

(i) DVS 0 to 90 to 0% RH (dm/dt<0.002%): 0.0 (0.0004%), 5.0 (0.0627%),10.0 (0.0957%), 15.0 (0.1397%), 20.0 (0.1778%), 25.0 (0.2093%), 30.0(0.2401%), 40.0 (0.3145%), 50.0 (0.4051%), 60.0 (0.5029%), 70.0(0.5451%), 80.0 (0.6660%), 90.0 (0.9766%), 90.0 (0.9766%), 80.0(0.6827%), 70.0 (0.5442%), 60.0 (0.4515%), 50.0 (0.3797%), 40.0(0.3210%), 30.0 (0.2656%), 25.0 (0.2387%), 20.0 (0.2126%), 15.0(0.1857%), 10.0 (0.1551%), 5.0 (0.1179%), 0.0 (0.0381%) (8-A4)as shownin FIG. 78 ;

(j) a UV chromatographic purity of 99.04% area (212 nm) as shown in FIG.151 ;

(k) an ¹H NMR: (DMSO-d6, 400 MHz); δ 10.6 (s, 1H), 7.3 (d, J=8.6 Hz,1H), 6.8 (s, 1H), 6.6 (dd, J=8.6, 2.2 Hz, 1H), 6.5 (s, 2H), 3.7 (s, 3H),3.1-3.0 (m, 6H), 2.9 (t, J=9.9, 5.6 Hz, 2H), 2.6 (s, 3H) conforms to themolecular structure (Σ20H) as shown in FIG. 146 ;

(l) an appearance as shown in FIG. 152 -FIG. 155 ;

(m) a crystal data as shown in FIG. 285 when collected using SingleCrystal XRD; and

(n) soluble in FaSSIF, FeSSIF and FaSSGF at 37° C. up to 24 h.

In some embodiments, the tabernanthalog monofumarate salt has Pattern#6a (Form A) and has a crystal data as shown in FIG. 285 when collectedusing Single Crystal XRD.

In some embodiments, the tabernanthalog monofumarate salt has Pattern#6a (Form A) and has a crystal data when collected using Single CrystalXRD as follows: C₁₈H₂₂N₂O₅, M_(r)=346.37, monoclinic, P2_(1/c) (No. 14),a=7.43280(10)Å, b=8.59740(10)Å, c=27.5143(3)Å, 8=96.6990(10°), α=γ=90°,V=1746.24(4) Å³, T=300(2) K, Z=4, Z′=1, u(Cu K)=0.801 mm⁻¹, 32845reflections measured, 3622 unique (R_(int)=0.0333) which were used inall calculations. The final wR₂ was 0.1071 (all data) and R₁ was 0.0409(I≥2σ(I)).

In some embodiments, Form A of the tabernanthalog monofumarate salt isobtained from suspension equilibration of the tabernanthalog fumaratesalt in water (5 vol) at 90° C. and the product is isolated byfiltration and dried under sustained nitrogen flux (<1 bar) over 20 h at20° C.

In some embodiments, Form A of the tabernanthalog monofumarate salt isobtained from suspension equilibration of the tabernanthalog fumaratesalt in water (5 vol) at 20° C. and the product is isolated byfiltration and dried under sustained nitrogen flux (<1 bar) over 20 h at20° C.

In some embodiments, the tabernanthalog monofumarate salt has Pattern#2a (Form B) and is characterized by at least one of the followingproperties:

(a) 33.5% w/w th. of fumaric acid;

(b) one or more, or two or more, or three or more XRPD signals selectedfrom the group consisting of 9.1°, 12.3°, 14.2°, 15.7°, 16.4°, 17.1°,17.4°, 18.1°, 18.8°, 20.7°, 21.0°, 22.3°, 22.8°, 23.0°, 24.7°, 25.0°,25.6°, 26.8°, 27.3°, 2θ, 1 d.p), (A1272-022-B2) as shown in FIG. 3 ; (c)a DSC profile exhibiting onsets at 100.6° C. (−0.74 Jg⁻¹, endotherm),125.7° C. (−1.57 Jg⁻¹, endotherm), and 174.1° C. (−31.27 Jg⁻¹,endotherm, melt) as shown in FIG. 316 ; (d) a TGA profile exhibitingonsets at 219.0° C. (−10.3% w/w, ablation), 286.8° C. (−1.9% w/w,ablation), and 324.6° C. (−2.5% w/w, ablation) as shown in FIG. 315 ;

(e) an ¹H NMR: (DMSO-d6, 400 MHz); δ 10.6 (s, 1H), 7.3 (d, J=8.6 Hz,1H), 6.8 (s, 1H), 6.6 (dd, J=8.6, 2.2 Hz, 1H), 6.5 (s, 2H), 3.7 (s, 3H),3.1-3.0 (m, 6H), 2.9 (t, J=9.9, 5.6 Hz, 2H), 2.6 (s, 3H) conforms to themolecular structure (Σ20H) as shown in FIG. 313 ); and

(f) Residual solvents ICH Q2C (R8): acetonitrile (0.1% w/w (0.03% w/w,ICH listed 10 ppm).

In some embodiments, Form B of the tabernanthalog monofumarate salt isobtained from suspension equilibration of the tabernanthalog fumaratesalt in acetonitrile (5 vol) at 40° C. and the product is isolated bycentrifugation and oven-dried under vacuum over 20 h at 40° C.

In some embodiments, the tabernanthalog hemifumarate salt has Pattern#14 (Form I) and is characterized by at least one of the followingproperties:

(a) 20.1% w/w th. of fumaric acid;

(b) a hydrogen bonding network wherein the fumaric acid is situatedin-between two molecules of Tabernanthalog via hydrogen bonds to theazepine (N1----O2, 2.70 Å) and indole nitrogen atoms (N2----O3, 2.81 Å)as shown in FIG. 292 ;

(c) monoclinic crystal system 300(2) with C2/c space group 300(2);

(d) a unit cell 300(2) K: a=21.7386(8)Å, b=9.7033(5)Å, c=15.8640(8)Å,a=g=90°, b=99.182(4)°, V=3303.4(3) Å³;

(e) an asymmetric unit which contained one molecule of API and halfmolecule of fumaric acid (crystal bonded);

(f) one or more, or two or more, or three or more XRPD signals selectedfrom the group consisting of 8.2°, 11.2°, 12.8°, 15.5°, 17.0°, 18.1°,18.3°, 19.2°, 19.4°, 20.2°, 21.3°, 21.5°, 22.6°, 23.7°, 24.3°, 24.8°,(2θ, 1 d.p) as shown in FIG. 377F;

(g) a DSC profile exhibiting onsets at 50.1° C. (−22.64 Jg⁻¹,endotherm), 115.1° C. (−22.28 Jg⁻¹, endotherm), 183° C. (−14.73 Jg⁻¹,endotherm), and 210.7 (−111.8 Jg⁻¹, endotherm, melt) as shown in FIG.377J;

(h) a TGA profile exhibiting onsets at 75.9° C. (−1.2% w/w, solventrelease), 141.5° C. (−1.3% w/w, solvent release), and 224.0° C. (−23.6%w/w, ablation) as shown in FIG. 377I;

(i) an ¹H NMR: (DMSO-d6, 400 MHz); δ 10.6 (s, 1H), 7.3 (d, J=8.6 Hz,1H), 6.8 (s, 1H), 6.6 (dd, J=8.6, 2.2 Hz, 1H), 6.5 (s, 2H), 3.7 (s, 3H),3.1-3.0 (m, 6H), 2.9 (t, J=9.9, 5.6 Hz, 2H), 2.6 (s, 3H) conforms to themolecular structure (Σ20H*) as shown in FIG. 377E (*The molecularformula (C₁₈H₂₂N₂O₅) includes the carboxylic acid protons; however, theyco-resonate with water.);

(j) Residual solvents: 5-B3 (acetonitrile 0.3% w/w, ICH listed 410 ppm,acetone 0.2% w/w, ICH listed 5000 ppm and methanol, 2.4% w/w, ICH listed3000 ppm).

and

(k) a crystal data as shown in FIG. 286 when collected using singleCrystal XRD.

In some embodiments, the tabernanthalog hemifumarate salt has Pattern#14 (Form I) and has a crystal data as shown in FIG. 286 when collectedusing single Crystal XRD.

In some embodiments, the tabernanthalog hemifumarate salt has Pattern#14 (Form I) and has a crystal data when collected using Single CrystalXRD as follows: C_(8.12)H_(10.5)NO_(1.62), M_(r)=148.17, monoclinic,C2/c (No. 15), a=21.7386(8)Å, b=9.7033(5)Å, c=15.8640(8)Å, β=99.182(4°),α=γ=90°, V=3303.4(3) Å³, T=300(2) K, Z=16, Z′=2, p(Cu Kα)=0.680 mm⁻¹,11278 reflections measured, 3227 unique (R_(int)=0.0472) which were usedin all calculations. The final wR₂ was 0.2751 (all data) and R₁ was0.0857 (1≥2σ(I)).

In some embodiments, Form I of the the tabernanthalog hemifumarate saltis obtained from dissolution of Tabernanthalog (native); TBG Native andfumaric acid (0.5 equiv) in methanol (20 vol).

In some embodiments, the tabernanthalog fumarate salt Form A (unaryfumarate, Pattern #6a), is prepared from water (anhydrous form,generated via suspension equilibration in water at 20° C.).

In some embodiments, in the presence of Form A, Form B slowly evolvesinto Form A under competitive suspension equilibration conditions.

In some embodiments, metastable forms obtained via suspensionequilibration and wet pellets, readily undergo conversion into Form Aduring drying.

In some embodiments, Form A exhibits greatest relative stability amongstother forms of the tabernanthalog fumarate salt.

In some embodiments, the hemi-fumarate salt of the tabernanthalogfumarate salt is prepared and re-proportionated into the fumarate saltduring an ageing cycle.

In some embodiments, stability assessment of the supplied material(Pattern #1) at 40° C./75% RH executed over a 4-to-5-week period showsno evidence for hydrate formation, chemical degradation ordisproportionation of the API.

Tabernanthalog Sorbate Salt

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 5.7°2θ, 11.4°2θ, and 22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized byXRPD signals at 5.7°2θ, 11.4°2θ, and 22.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt (FormA) is characterized by one, two, or three XRPD signals selected fromthose set forth in Table 273.

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.5°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by XRPD signals at5.7°2θ, 11.5°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by XRPD signals at5.7°2θ, 11.5°2θ, 18.9°2θ, 22.8°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by XRPD signals at5.7°2θ, 10.6°2θ, 11.5°2θ, 18.9°2θ, 22.8°2θ, 24.5°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, or seven XRPD signalsselected from those set forth in Table 274.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #1) is crystalline tabernanthalog sorbate (Pattern #1)characterized by one or more XRPD signals selected from the groupconsisting of 7.5°2θ and 15.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #1) is crystalline tabernanthalog sorbate (Pattern #1)characterized by XRPD signals at 7.5°2θ and 15.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one or two XRPD signals selected from those set forthin Table 276.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #1) is crystalline tabernanthalog sorbate (Pattern #1)characterized by one or more XRPD signals selected from the groupconsisting of 7.6°2θ and 15.1°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #1) is crystalline tabernanthalog sorbate (Pattern #1)characterized by XRPD signals at 7.6°2θ and 15.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one or two XRPD signals selected from those set forthin Table 277.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #2) is crystalline tabernanthalog sorbate (Pattern #2)characterized by one or more XRPD signals selected from the groupconsisting of 5.7°2θ and 11.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #2) is crystalline tabernanthalog sorbate (Pattern #2)characterized by XRPD signals at 5.7°2θ and 11.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one or two XRPD signals selected from those set forthin Table 279.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #2) is crystalline tabernanthalog sorbate salt (Pattern #2)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 5.7°2θ, 16.7°2θ, and 22.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #2) is crystalline tabernanthalog sorbate salt (Pattern #2)characterized by XRPD signals at 5.7°2θ, 16.7°2θ, and 22.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #2) is crystalline tabernanthalog sorbate salt (Pattern #2)characterized by XRPD signals at 5.7°2θ, 11.5°2θ, 16.7°2θ, 17.3°2θ, and22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #2) is crystalline tabernanthalog sorbate salt (Pattern #2)characterized by XRPD signals at 5.7°2θ, 11.5°2θ, 16.7°2θ, 17.3°2θ,18.5°2θ, 18.7°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #2) is crystalline tabernanthalog sorbate salt (Pattern #2)characterized by XRPD signals at 5.7°2θ, 11.2°2θ, 11.5°2θ, 16.7°2θ,17.3°2θ, 17.8°2θ, 18.5°2θ, 18.7°2θ, 20.1°2θ, and 22.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten XRPD signals selected from those set forth in Table 280.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #3) is crystalline tabernanthalog sorbate salt (Pattern #3)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 5.7°2θ, 7.3°2θ, and 11.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #3) is crystalline tabernanthalog sorbate salt (Pattern #3)characterized by XRPD signals at 5.7°2θ, 7.3°2θ, and 11.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #3) is crystalline tabernanthalog sorbate salt (Pattern #3)characterized by XRPD signals at 5.7°2θ, 7.3°2θ, 7.4°2θ, 11.5°2θ, and18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #3) is crystalline tabernanthalog sorbate salt (Pattern #3)characterized by XRPD signals at 5.7°2θ, 7.3°2θ, 7.4°2θ, 11.5°2θ,18.9°2θ, 24.7°2θ, and 24.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #3) is crystalline tabernanthalog sorbate salt (Pattern #3)characterized by XRPD signals at 5.7°2θ, 7.3°2θ, 7.4°2θ, 10.6°2θ,11.5°2θ, 18.9°2θ, 23.0°2θ, 24.7°2θ, 24.8°2θ, and 29.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten XRPD signals selected from those set forth in Table 282.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #4) is crystalline tabernanthalog sorbate salt (Pattern #4)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 5.8°2θ, 5.9°2θ, and 22.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #4) is crystalline tabernanthalog sorbate salt (Pattern #4)characterized by XRPD signals at 5.8°2θ, 5.9°2θ, and 22.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #4) is crystalline tabernanthalog sorbate salt (Pattern #4)characterized by XRPD signals at 5.8°2θ, 5.9°2θ, 16.8°2θ, 18.6°2θ, and22.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #4) is crystalline tabernanthalog sorbate salt (Pattern #4)characterized by XRPD signals at 5.8°2θ, 5.9°2θ, 11.6°2θ, 16.8°2θ,17.5°2θ, 18.6°2θ, and 22.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #4) is crystalline tabernanthalog sorbate salt (Pattern #4)characterized by XRPD signals at 5.8°2θ, 5.9°2θ, 11.3°2θ, 11.6°2θ,16.8°2θ, 17.5°2θ, 17.9°2θ, 18.6°2θ, 18.8°2θ, and 22.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten XRPD signals selected from those set forth in Table 284.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #5) is crystalline tabernanthalog sorbate salt (Pattern #5)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 14.1°2θ, 16.5°2θ, and 20.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #5) is crystalline tabernanthalog sorbate salt (Pattern #5)characterized by XRPD signals at 14.1°2θ, 16.5°2θ, and 20.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #5) is crystalline tabernanthalog sorbate salt (Pattern #5)characterized by XRPD signals at 14.1°2θ, 16.5°2θ, 20.5°2θ, 20.8°2θ, and21.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #5) is crystalline tabernanthalog sorbate salt (Pattern #5)characterized by XRPD signals at 14.1°2θ, 16.5°2θ, 18.3°2θ, 20.5°2θ,20.8°2θ, 21.2°2θ, and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #5) is crystalline tabernanthalog sorbate salt (Pattern #5)characterized by XRPD signals at 7.7°2θ, 14.1°2θ, 16.5°2θ, 18.3°2θ,19.2°2θ, 20.5°2θ, 20.8°2θ, 21.2°2θ, 23.2°2θ, and 27.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten XRPD signals selected from those set forth in Table 286.

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #6) is crystalline tabernanthalog sorbate (Pattern #6)characterized by one or more XRPD signals selected from the groupconsisting of 7.2°2θ and 5.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt(Pattern #6) is crystalline tabernanthalog sorbate (Pattern #6)characterized by XRPD signals at 7.2°2θ and 5.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one or two XRPD signals selected from those set forthin Table 288.

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 5.7°2θ, 11.4°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized byXRPD signals at 5.7°2θ, 11.4°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized byXRPD signals at 5.7°2θ, 11.4°2θ, 22.6°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, or four XRPD signals selected fromthose set forth in Table 289.

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.1°2θ, 21.8°2θ, and 25.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by XRPD signals at18.1°2θ, 21.8°2θ, and 25.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt (characterized by XRPD signalsat 17.9°2θ, 18.1°2θ, 20.1°2θ, 21.8°2θ, and 25.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by XRPD signals at17.9°2θ, 18.1°2θ, 18.7°2θ, 20.1°2θ, 21.8°2θ, 25.0°2θ, and29.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate salt characterized by XRPD signals at12.5°2θ, 17.9°2θ, 18.1°2θ, 18.7°2θ, 20.1°2θ, 21.8°2θ, 25.0°2θ, 26.0°2θ,27.5°2θ, and 29.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten XRPD signals selected from those set forth in Table 290.

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized bytwo or more, or three or more XRPD signals selected from the groupconsisting of 5.7°2θ, 11.5°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized byXRPD signals at 5.7°2θ, 11.5°2θ, and 23.0 °2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt (FormA) is crystalline tabernanthalog sorbate salt (Form A) characterized byXRPD signals at 5.7°2θ, 11.5°2θ, 18.8°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt (FormA) is characterized by one, two, three, or four XRPD signals selectedfrom those set forth in Table 291.

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.5°2θ, and 17.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogsorbate Form A is crystalline tabernanthalog sorbate Form Acharacterized by XRPD signals at 18.9°2θ, 24.5°2θ, and 17.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.5°2θ, 17.9°2θ, 22.6°2θ, and 5.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate Form A is crystalline tabernanthalog sorbate FormA characterized by XRPD signals at 18.9°2θ, 24.5°2θ, 17.9°2θ, 22.6°2θ,and 5.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.5°2θ, 17.9°2θ, 22.6°2θ, 5.6°2θ, 17.4°2θ, and11.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by XRPD signalsat 18.9°2θ, 24.5°2θ, 17.9°2θ, 22.6°2θ, 5.6°2θ, 17.4°2θ, and11.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.5°2θ, 17.9°2θ, 22.6°2θ, 5.6°2θ, 17.4°2θ, 11.3°2θ, 10.5°2θ,21.4°2θ, and 26.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by XRPD signalsat 18.9°2θ, 24.5°2θ, 17.9°2θ, 22.6°2θ, 5.6°2θ, 17.4°2θ, 11.3°2θ,10.5°2θ, 21.4°2θ, and 26.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog sorbate Form A ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPDsignals selected from those set forth in Table 317.

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.6°2θ, and 24.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogsorbate Form A is crystalline tabernanthalog sorbate Form Acharacterized by XRPD signals at 18.9°2θ, 24.6°2θ, and 24.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.6°2θ, 24.5°2θ, 19.1°2θ, and 17.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate Form A is crystalline tabernanthalog sorbate FormA characterized by XRPD signals at 18.9°2θ, 24.6°2θ, 24.5°2θ, 19.1°2θ,and 17.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.6°2θ, 24.5°2θ, 19.1°2θ, 17.9°2θ, 22.6°2θ, and5.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by XRPD signalsat 18.9°2θ, 24.6°2θ, 24.5°2θ, 19.1°2θ, 17.9°2θ, 22.6°2θ, and5.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 24.6°2θ, 24.5°2θ, 19.1°2θ, 17.9°2θ, 22.6°2θ, 5.6°2θ, 21.4°2θ,10.5°2θ, and 11.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by XRPD signalsat 18.9°2θ, 24.6°2θ, 24.5°2θ, 19.1°2θ, 17.9°2θ, 22.6°2θ, 5.6°2θ,21.4°2θ, 10.5°2θ, and 11.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog sorbate Form A ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, oreighteen XRPD signals selected from those set forth in Table 318.

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogsorbate Form A is crystalline tabernanthalog sorbate Form Acharacterized by XRPD signals at 18.9°2θ, 5.7°2θ, and 24.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 24.7°2θ, 24.5°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate Form A is crystalline tabernanthalog sorbate FormA characterized by XRPD signals at 18.9°2θ, 5.7°2θ, 24.7°2θ, 24.5°2θ,and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 24.7°2θ, 24.5°2θ, 10.5°2θ, 11.4°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of tabernanthalog sorbate Form A is crystallinetabernanthalog sorbate Form A characterized by XRPD signals at 18.9°2θ,5.7°2θ, 24.7°2θ, 24.5°2θ, 10.5°2θ, 11.4°2θ, and 22.6°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 24.7°2θ, 24.5°2θ, 10.5°2θ, 11.4°2θ, 22.6°2θ, 17.9°2θ,19.1°2θ, and 21.4°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by XRPD signalsat 18.9°2θ, 5.7°2θ, 24.7°2θ, 24.5°2θ, 10.5°2θ, 11.4°2θ, 22.6°2θ,17.9°2θ, 19.1°2θ, and 21.4°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog sorbate Form A ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, or nineteen XRPD signals selected from those set forth inTable 319.

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.7°2θ, 24.5°2θ, and 22.5°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at18.7°2θ, 24.5°2θ, and 22.5°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.7°2θ, 24.5°2θ, 22.5°2θ, 11.2°2θ, and 24.2°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate is crystalline tabernanthalog sorbatecharacterized by XRPD signals at 18.7°2θ, 24.5°2θ, 22.5°2θ, 11.2°2θ, and24.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.7°2θ, 24.5°2θ, 22.5°2θ, 11.2°2θ, 24.2°2θ, 22.8°2θ, and19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog sorbate is crystallinetabernanthalog sorbate characterized by XRPD signals at 18.7°2θ,24.5°2θ, 22.5°2θ, 11.2°2θ, 24.2°2θ, 22.8°2θ, and 19.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.7°2θ, 24.5°2θ, 22.5°2θ, 11.2°2θ, 24.2°2θ, 22.8°2θ, 19.0°2θ, 21.3°2θ,17.9°2θ, and 26.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at18.7°2θ, 24.5°2θ, 22.5°2θ, 11.2°2θ, 24.2°2θ, 22.8°2θ, 19.0°2θ, 21.3°2θ,17.9°2θ, and 26.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, or twenty-one XRPD signals selected fromthose set forth in Table 320.

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.4°2θ, 6.3°2θ, and 19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·Pattern #7 is crystallineTabernanthalog·Sorbate·Pattern #7 characterized by XRPD signals at9.4°2θ, 6.3°2θ, and 19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.4°2θ, 6.3°2θ, 19.0°2θ, 22.6°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·Pattern #7 is crystallineTabernanthalog·Sorbate·Pattern #7 characterized by XRPD signals at9.4°2θ, 6.3°2θ, 19.0°2θ, 22.6°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.4°2θ, 6.3°2θ, 19.0°2θ, 22.6°2θ, 17.7°2θ, 17.1°2θ, and15.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7 iscrystalline Tabernanthalog·Sorbate·Pattern #7 characterized by XRPDsignals at 9.4°2θ, 6.3°2θ, 19.0°2θ, 22.6°2θ, 17.7°2θ, 17.1°2θ, and15.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.4°2θ, 6.3°2θ, 19.0°2θ, 22.6°2θ, 17.7°2θ, 17.1°2θ, 15.8°2θ, 19.4°2θ,15.4°2θ, and 17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7 iscrystalline Tabernanthalog·Sorbate·Pattern #7 characterized by XRPDsignals at 9.4°2θ, 6.3°2θ, 19.0°2θ, 22.6°2θ, 17.7°2θ, 17.1°2θ, 15.8°2θ,19.4°2θ, 15.4°2θ, and 17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the crystalline Tabernanthalog·Sorbate·Pattern #7is characterized by one, two, three, four, five, six, seven, eight,nine, ten, or eleven XRPD signals selected from those set forth in Table322.

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.5°2θ, 19.0°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·Pattern #7 is crystallineTabernanthalog·Sorbate·Pattern #7 characterized by XRPD signals at9.5°2θ, 19.0 °2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.5°2θ, 19.0°2θ, 22.6°2θ, 6.4°2θ, and 15.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·Pattern #7 is crystallineTabernanthalog·Sorbate·Pattern #7 characterized by XRPD signals at9.5°2θ, 19.0°2θ, 22.6°2θ, 6.4°2θ, and 15.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.5°2θ, 19.0°2θ, 22.6°2θ, 6.4°2θ, 15.4°2θ, 17.7°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7 iscrystalline Tabernanthalog·Sorbate·Pattern #7 characterized by XRPDsignals at 9.5°2θ, 19.0°2θ, 22.6°2θ, 6.4°2θ, 15.4°2θ, 17.7°2θ, and17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 9.5°2θ, 19.0°2θ, 22.6°2θ, 6.4°2θ, 15.4°2θ, 17.7°2θ, 17.1°2θ, 17.2°2θ,19.5°2θ, and 13.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7 iscrystalline Tabernanthalog·Sorbate·Pattern #7 characterized by XRPDsignals at 9.5°2θ, 19.0°2θ, 22.6°2θ, 6.4°2θ, 15.4°2θ, 17.7°2θ, 17.1°2θ,17.2°2θ, 19.5°2θ, and 13.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the crystalline Tabernanthalog·Sorbate·Pattern #7is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, or twenty-one XRPD signalsselected from those set forth in Table 323.

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 22.7°2θ, 17.7°2θ, and 17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·Pattern #7 is crystallineTabernanthalog·Sorbate·Pattern #7 characterized by XRPD signals at22.7°2θ, 17.7°2θ, and 17.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 22.7°2θ, 17.7°2θ, 17.2°2θ, 9.5°2θ, and 19.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·Pattern #7 is crystallineTabernanthalog·Sorbate·Pattern #7 characterized by XRPD signals at22.7°2θ, 17.7°2θ, 17.2°2θ, 9.5°2θ, and 19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 22.7°2θ, 17.7°2θ, 17.2°2θ, 9.5°2θ, 19.0°2θ, 15.4°2θ, and13.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7 iscrystalline Tabernanthalog·Sorbate·Pattern #7 characterized by XRPDsignals at 22.7°2θ, 17.7°2θ, 17.2°2θ, 9.5°2θ, 19.0°2θ, 15.4°2θ, and13.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7is crystalline Tabernanthalog·Sorbate·Pattern #7 characterized by two ormore, or three or more XRPD signals selected from the group consistingof 22.7°2θ, 17.7°2θ, 17.2°2θ, 9.5°2θ, 19.0°2θ, 15.4°2θ, 13.3°2θ, 6.3°2θ,19.5°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of Tabernanthalog·Sorbate·Pattern #7 iscrystalline Tabernanthalog·Sorbate·Pattern #7 characterized by XRPDsignals at 22.7°2θ, 17.7°2θ, 17.2°2θ, 9.5°2θ, 19.0°2θ, 15.4°2θ, 13.3°2θ,6.3°2θ, 19.5°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the crystalline Tabernanthalog·Sorbate·Pattern #7is characterized by one, two, three, four, five, six, seven, eight,nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, ortwenty-three XRPD signals selected from those set forth in Table 324.

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of5.7°2θ, 18.9°2θ, and 31.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogsorbate Form A is crystalline tabernanthalog sorbate Form Acharacterized by XRPD signals at 5.7°2θ, 18.9°2θ, and 31.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of5.7°2θ, 18.9°2θ, 31.7°2θ, 24.7°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate Form A is crystalline tabernanthalog sorbate FormA characterized by XRPD signals at 5.7°2θ, 18.9°2θ, 31.7°2θ, 24.7°2θ,and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of5.7°2θ, 18.9°2θ, 31.7°2θ, 24.7°2θ, 10.5°2θ, 18.0°2θ, and22.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by XRPD signalsat 5.7°2θ, 18.9°2θ, 31.7°2θ, 24.7°2θ, 10.5°2θ, 18.0°2θ, and22.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by two or more,or three or more XRPD signals selected from the group consisting of5.7°2θ, 18.9°2θ, 31.7°2θ, 24.7°2θ, 10.5°2θ, 18.0°2θ, 22.7°2θ, 11.4°2θ,19.2°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog sorbate Form A iscrystalline tabernanthalog sorbate Form A characterized by XRPD signalsat 5.7°2θ, 18.9°2θ, 31.7°2θ, 24.7°2θ, 10.5°2θ, 18.0°2θ, 22.7°2θ,11.4°2θ, 19.2°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog sorbate Form A ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, or twenty XRPD signals selected from those set forthin Table 325.

In some embodiments, the solid form of Tabernanthalog·Sorbate HemiHFIPA(pattern #7) is crystalline Tabernanthalog·Sorbate HemiHFIPA (pattern#7) characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 22.6°2θ, 9.4°2θ, and 17.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform Tabernanthalog·Sorbate HemiHFIPA (pattern #7) is crystallineTabernanthalog·Sorbate HemiHFIPA (pattern #7)characterized by XRPDsignals at 22.6°2θ, 9.4°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate HemiHFIPA(pattern #7)is crystalline Tabernanthalog·Sorbate HemiHFIPA (pattern #7)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 22.6°2θ, 9.4°2θ, 17.7°2θ, 17.1°2θ, and19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog·Sorbate HemiHFIPA (pattern#7) is crystalline Tabernanthalog·Sorbate HemiHFIPA (pattern #7)characterized by XRPD signals at 22.6°2θ, 9.4°2θ, 17.7°2θ, 17.1°2θ, and19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate HemiHFIPA(pattern #7)salt is crystalline Tabernanthalog·Sorbate HemiHFIPA(pattern #7) characterized by two or more, or three or more XRPD signalsselected from the group consisting of 22.6°2θ, 9.4°2θ, 17.7°2θ, 17.1°2θ,19.0°2θ, 6.3°2θ, and 15.4°2θ, (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate HemiHFIPA (pattern #7)is crystallineTabernanthalog·Sorbate HemiHFIPA (pattern #7) characterized by XRPDsignals at 22.6°2θ, 9.4°2θ, 17.7°2θ, 17.1°2θ, 19.0°2θ, 6.3°2θ, and15.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate HemiHFIPA(pattern #7)is crystalline Tabernanthalog·Sorbate HemiHFIPA (pattern#7)characterized by two or more, or three or more XRPD signals selectedfrom the group consisting of 22.6°2θ, 9.4°2θ, 17.7°2θ, 17.1°2θ, 19.0°2θ,6.3°2θ, 15.4°2θ, 17.1°2θ, 19.4°2θ, 13.3°2θ, and 23.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solidform of Tabernanthalog·Sorbate HemiHFIPA (pattern #7) isTabernanthalog·Sorbate HemiHFIPA (pattern #7) characterized by XRPDsignals at 22.6°2θ, 9.4°2θ, 17.7°2θ, 17.1°2θ, 19.0°2θ, 6.3°2θ, 15.4°2θ,17.1°2θ, 19.4°2θ, 13.3°2θ, and 23.8°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline Tabernanthalog·Sorbate HemiHFIPA(pattern #7)is characterized by one, two, three, four, five, six, seven,eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen,seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two,twenty-three, twenty-four XRPD signals selected from those set forth inTable 303.

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or moreXRPD signals selected from the group consisting of 5.7°2θ, 11.4°2θ, and24.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals5.7°2θ, 11.4°2θ, and 24.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 24.6°2θ, 24.5°2θ, and 18.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of Tabernanthalogsorbate salt is crystalline Tabernanthalog sorbate salt characterized byXRPD signals at 5.7°2θ, 11.4°2θ, 24.6°2θ, 24.5°2θ, and 18.9°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, or six XRPD signalsselected from those set forth in Table 304.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.6°2θ,11.3°2θ, and 18.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals at5.6°2θ, 11.3°2θ, and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, or three XRPD signals selected from those setforth in Table 305.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals at5.7°2θ, 11.4°2θ, and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 18.9°2θ, 24.7°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of Tabernanthalogsorbate salt is crystalline Tabernanthalog sorbate salt characterized byXRPD signals at 5.7°2θ, 11.4°2θ, 18.9°2θ, 24.7°2θ, and 10.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 18.9°2θ, 24.7°2θ, 10.5°2θ, 22.7°2θ, and 18.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of Tabernanthalog sorbate salt is crystalline Tabernanthalogsorbate salt characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 18.9°2θ,24.7°2θ, 10.5°2θ, 22.7°2θ, and 18.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 18.9°2θ, 24.7°2θ, 10.5°2θ, 22.7°2θ, 18.0°2θ, 24.4°2θ, 19.2°2θ,and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals at5.7°2θ, 11.4°2θ, 18.9°2θ, 24.7°2θ, 10.5°2θ, 22.7°2θ, 18.0 °2θ, 24.4°2θ,19.2°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,or ten, XRPD signals selected from those set forth in Table 306.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 18.9°2θ, 22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of Tabernanthalogsorbate salt is crystalline Tabernanthalog sorbate salt characterized byXRPD signals at 5.7°2θ, 11.4°2θ, 18.9°2θ, 22.8°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, or four XRPD signals selected fromthose set forth in Table 307.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by one or two XRPDsignals selected from the group consisting of 5.7°2θ, and 11.4°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of Tabernanthalog sorbate salt is crystallineTabernanthalog sorbate salt characterized by XRPD signals at 5.7°2θ, and11.4°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one or two XRPD signals selected from those set forthin Table 308.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.5°2θ, 22.7°2θ, and 7.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form Tabernanthalog sorbatesalt is crystalline Tabernanthalog sorbate salt characterized by XRPDsignals at 22.5°2θ, 22.7°2θ, and 7.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.5°2θ, 22.7°2θ, 7.6°2θ, 5.7°2θ, and 22.6°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog sorbate salt is crystalline Tabernanthalog sorbate saltcharacterized by XRPD signals at 22.5°2θ, 22.7°2θ, 7.6°2θ, 5.7°2θ, and22.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.5°2θ, 22.7°2θ, 7.6°2θ, 5.7°2θ, 22.6°2θ, 17.1°2θ, and 13.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of Tabernanthalog sorbate salt is crystallineTabernanthalog sorbate salt characterized by XRPD signals at 22.5°2θ,22.7°2θ, 7.6°2θ, 5.7°2θ, 22.6°2θ, 17.1°2θ, and 13.3°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.5°2θ, 22.7°2θ, 7.6°2θ, 5.7°2θ, 22.6°2θ, 17.1°2θ, 13.3°2θ, 15.4°2θ,9.5°2θ, and 11.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals at22.5°2θ, 22.7°2θ, 7.6°2θ, 5.7°2θ, 22.6°2θ, 17.1°2θ, 13.3°2θ, 15.4°2θ,9.5°2θ, and 11.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, ortwenty-four XRPD signals selected from those set forth in Table 309.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).In some embodiments, the solid form Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals5.7°2θ, 18.9°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, 24.7°2θ, 11.4°2θ, and 24.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of Tabernanthalogsorbate salt is crystalline Tabernanthalog sorbate salt characterized byXRPD signals at 5.7°2θ, 18.9°2θ, 24.7°2θ, 11.4°2θ, and 24.5°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, 24.7°2θ, 11.4°2θ, 24.5°2θ, 10.5°2θ, and 22.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of Tabernanthalog sorbate salt is crystalline Tabernanthalogsorbate salt characterized by XRPD signals at 5.7°2θ, 18.9°2θ, 24.7°2θ,11.4°2θ, 24.5°2θ, 10.5°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, 24.7°2θ, 11.4°2θ, 24.5°2θ, 10.5°2θ, 22.6°2θ, 19.1°2θ, 17.9°2θ,and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals at5.7°2θ, 18.9°2θ, 24.7°2θ, 11.4°2θ, 24.5°2θ, 10.5°2θ, 22.6°2θ, 19.1°2θ,17.9°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, ortwenty-four XRPD signals selected from those set forth in Table 310.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of Tabernanthalogsorbate salt is crystalline Tabernanthalog sorbate salt characterized byXRPD signals at 18.9°2θ, 5.7°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 10.5°2θ, 15.1°2θ, and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog sorbate salt is crystalline Tabernanthalog sorbate saltcharacterized by XRPD signals at 18.9°2θ, 5.7°2θ, 10.5°2θ, 15.1°2θ, and27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 10.5°2θ, 15.1°2θ, 27.4°2θ, 18.0°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of Tabernanthalog sorbate salt is crystallineTabernanthalog sorbate salt characterized by XRPD signals at 18.9°2θ,5.7°2θ, 10.5°2θ, 15.1°2θ, 27.4°2θ, 18.0°2θ, and 24.7°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, or seven XRPD signalsselected from those set forth in Table 311.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).In some embodiments, the solid form Tabernanthalog sorbate salt salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals5.7°2θ, 18.9°2θ, and 10.5°2θ°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, 10.5°2θ, 11.5°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of Tabernanthalogsorbate salt is crystalline Tabernanthalog sorbate salt characterized byXRPD signals at 5.7°2θ, 18.9°2θ, 10.5°2θ, 11.5°2θ, and 24.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt scrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, 10.5°2θ, 11.5°2θ, 24.7°2θ, 18.0°2θ, 24.6°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog sorbate salt is crystalline Tabernanthalog sorbate saltcharacterized by XRPD signals at 5.7°2θ, 18.9°2θ, 10.5°2θ, 11.5°2θ,24.7°2θ, 18.0°2θ, 24.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,18.9°2θ, 10.5°2θ, 11.5°2θ, 24.7°2θ, 18.0°2θ, 24.6°2θ, 19.2°2θ, 18.4°2θ,and 22.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals at5.7°2θ, 18.9°2θ, 10.5°2θ, 11.5°2θ, 24.7°2θ, 18.0 °2θ, 24.6°2θ, 19.2°2θ,18.4°2θ, and 22.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signalsselected from those set forth in Table 312.

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, and 24.7°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form Tabernanthalog sorbatesalt salt is crystalline Tabernanthalog sorbate salt characterized byXRPD signals 18.9°2θ, 5.7°2θ, and 24.7°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 24.7°2θ, 19.1°2θ, and 10.5°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog sorbate salt is crystalline Tabernanthalog sorbate saltcharacterized by XRPD signals at 18.9°2θ, 5.7°2θ, 24.7°2θ, 19.1°2θ, and10.5°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt scrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 24.7°2θ, 19.1°2θ, 10.5°2θ, 18.4°2θ, and 18°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of Tabernanthalog sorbate salt is crystalline Tabernanthalogsorbate salt characterized by XRPD signals at 18.9°2θ, 5.7°2θ, 24.7°2θ,19.1°2θ, 10.5°2θ, 18.4°2θ, and 18°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by two or more, orthree or more XRPD signals selected from the group consisting of18.9°2θ, 5.7°2θ, 24.7°2θ, 19.1°2θ, 10.5°2θ, 18.4°2θ, 18°2θ, 11.4°2θ,24.5°2θ, and 22.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of Tabernanthalog sorbate salt iscrystalline Tabernanthalog sorbate salt characterized by XRPD signals at18.9°2θ, 5.7°2θ, 24.7°2θ, 19.1°2θ, 10.5°2θ, 18.4°2θ, 18°2θ, 11.4°2θ,24.5°2θ, and 22.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeenXRPD signals selected from those set forth in Table 313.

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 16.3°2θ, 9.1°2θ, and 25.6°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form Tabernanthalogmonofumarate salt salt is crystalline Tabernanthalog monofumarate saltcharacterized by XRPD signals 16.3°2θ, 9.1°2θ, and 25.6°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 16.3°2θ, 9.1°2θ, 25.6°2θ, 19.3°2θ, and 26.8°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog monofumarate salt is crystalline Tabernanthalogmonofumarate salt characterized by XRPD signals at 16.3°2θ, 9.1°2θ,25.6°2θ, 19.3°2θ, and 26.8°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate salts crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 16.3°2θ, 9.1°2θ, 25.6°2θ, 19.3°2θ, 26.8°2θ, 25.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of Tabernanthalog monofumarate salt is crystallineTabernanthalog monofumarate salt characterized by XRPD signals at16.3°2θ, 9.1°2θ, 25.6°2θ, 19.3°2θ, 26.8°2θ, 25.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 16.3°2θ, 9.1°2θ, 25.6°2θ, 19.3°2θ, 26.8°2θ, 25.1°2θ, 16.7°2θ,18.1°2θ, 22.3°2θ, and 27.2°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of Tabernanthalogmonofumarate salt is crystalline Tabernanthalog monofumarate saltcharacterized by XRPD signals at 16.3°2θ, 9.1°2θ, 25.6°2θ, 19.3°2θ,26.8°2θ, 25.1°2θ, 16.7°2θ, 18.1°2θ, 22.3°2θ, and 27.2°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog monofumarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, or twelve XRPD signals selected from those set forth inTable 314.

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 7.4°2θ, 21.5°2θ, and 16.0°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form Tabernanthalogmonofumarate salt salt is crystalline Tabernanthalog monofumarate saltcharacterized by XRPD signals 7.4°2θ, 21.5°2θ, and 16.0°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 7.4°2θ, 21.5°2θ, 16.0°2θ, 20.3°2θ, and 25.7°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog monofumarate salt is crystalline Tabernanthalogmonofumarate salt characterized by XRPD signals at 7.4°2θ, 21.5°2θ,16.0°2θ, 20.3°2θ, and 25.7°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate salts crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 7.4°2θ, 21.5°2θ, 16.0°2θ, 20.3°2θ, 25.7°2θ, and 20.8°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of Tabernanthalog monofumarate salt is crystalline Tabernanthalogmonofumarate salt characterized by XRPD signals at 7.4°2θ, 21.5°2θ,16.0°2θ, 20.3°2θ, 25.7°2θ, and 20.8°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline Tabernanthalog monofumarate salt ischaracterized by one, two, three, four, five, or six XRPD signalsselected from those set forth in Table 315.

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 8.2°2θ, 11.2°2θ, and 17.1°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form Tabernanthalogmonofumarate salt is crystalline Tabernanthalog monofumarate saltcharacterized by XRPD signals 8.2°2θ, 11.2°2θ, and 17.1°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 8.2°2θ, 11.2°2θ, 17.1°2θ, 24.4°2θ, and 23.8°2θ (±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog monofumarate salt is crystalline Tabernanthalogmonofumarate salt characterized by XRPD signals at 8.2°2θ, 11.2°2θ,17.1°2θ, 24.4°2θ, and 23.8°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate salts crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 8.2°2θ, 11.2°2θ, 17.1°2θ, 24.4°2θ, 23.8°2θ, 21.5°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of Tabernanthalog monofumarate salt is crystallineTabernanthalog monofumarate salt characterized by XRPD signals at8.2°2θ, 11.2°2θ, 17.1°2θ, 24.4°2θ, 23.8°2θ, 21.5°2θ, and 20.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog monofumarate saltis crystalline Tabernanthalog monofumarate salt characterized by two ormore, or three or more XRPD signals selected from the group consistingof 8.2°2θ, 11.2°2θ, 17.1°2θ, 24.4°2θ, 23.8°2θ, 21.5°2θ, 20.2°2θ, and8.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog monofumarate salt iscrystalline Tabernanthalog monofumarate salt characterized by XRPDsignals at 8.2°2θ, 11.2°2θ, 17.1°2θ, 24.4°2θ, 23.8°2θ, 21.5°2θ, 20.2°2θ,and 8.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog monofumarate salt ischaracterized by one, two, three, four, five, six, seven, or eight XRPDsignals selected from those set forth in Table 316.

In some embodiments, Form A of the tabernanthalog sorbate salt isobtained from heat-up/cool-down crystallization of tabernanthalog(native) with sorbic acid in ethanol (5.0 vol) at 85° C. The product wasisolated by centrifugation and was oven-dried under reduced pressureover 20 h at 40° C.

In yet other embodiments, Form A of the tabernanthalog sorbate salt isobtained heat-up/cool-down crystallization of tabernanthalog (native)with sorbic acid in ethanol (3.0 vol) and the salt is isolated byfiltration and dried under sustained nitrogen flux (<1 bar) over 20 h at20° C.

In one embodiment, Form A of the tabernanthalog sorbate salt is a unarysorbate with 24.7% w/w th., sorbic acid (i.e., 1.0 mol of API to 1.0 molsorbic acid).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ,22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, 21.4°2θ, 17.9°2θ, and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ,22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, 21.4°2θ, and 17.9°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7 °2θ, 18.8°2θ,10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, and 21.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ,22.6°2θ, 24.4°2θ, 26.9°2θ, and 19.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ,22.6°2θ, 24.4°2θ, and 26.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ,22.6°2θ, and 24.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ,and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, and10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, 24.7°2θ, and18.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by two or more, or three XRPD signals selectedfrom the group consisting of 5.7°2θ, 11.4°2θ, and 24.7°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, 21.4°2θ, 17.9°2θ,and 22.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, 21.4°2θ, and17.9°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ, and21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ, and 19.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, and 26.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, and 24.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,and 18.8°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation).

In one embodiment, Form A of the tabernanthalog sorbate salt iscrystalline characterized by XRPD signals at 5.7°2θ, 11.4°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, Form A of the tabernanthalog sorbate salt iscrystalline characterized two or more, or three XRPD signals as shown inTable 216.

In some embodiments, Form A of the tabernanthalog sorbate salt iscrystalline characterized two or more, or three XRPD signals as shown inFIG. 384 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan ¹H NMR spectrum as depicted in FIG. 451 , FIG. 561 , or FIG. 562 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsa DSC profile as depicted in FIG. 453 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsa TGA profile as depicted in FIG. 454 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsa DVS profile as depicted in FIG. 455 or FIG. 456 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan XRPD pattern as depicted in FIG. 384 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan XRPD pattern post DVS as depicted in FIG. 458 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsan HPLC spectrum as depicted in FIG. 460 or FIG. 566 .

In some embodiments, Form A of the tabernanthalog sorbate salt exhibitsat least one property as listed in Table 192.

In some embodiments, the solid form of Tabernanthalog·Sorbate (Form A)is crystalline Tabernanthalog·Sorbate (Form A) characterized by two ormore, or three or more XRPD signals selected from the group consistingof 19.1°2θ, 25.0°2θ, and 5.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate (Form A) is crystalline Tabernanthalog·Sorbate(Form A) characterized by XRPD signals at 19.1°2θ, 25.0 °2θ, and5.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate (Form A)is crystalline Tabernanthalog·Sorbate (Form A) characterized by two ormore, or three or more XRPD signals selected from the group consistingof 19.1°2θ, 25.0°2θ, 5.8°2θ, 10.7°2θ, and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate (Form A) is crystalline Tabernanthalog·Sorbate(Form A) characterized by XRPD signals at 19.1°2θ, 25.0°2θ, 5.8°2θ,10.7°2θ, and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate (Form A)is crystalline Tabernanthalog·Sorbate (Form A) characterized by two ormore, or three or more XRPD signals selected from the group consistingof 19.1°2θ, 25.0°2θ, 5.8°2θ, 10.7°2θ, 22.9°2θ, 18.1°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of Tabernanthalog·Sorbate (Form A) iscrystalline Tabernanthalog·Sorbate (Form A) characterized by XRPDsignals at 19.1°2θ, 25.0°2θ, 5.8°2θ, 10.7°2θ, 22.9°2θ, 18.1°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate (Form A)is crystalline Tabernanthalog·Sorbate (Form A) characterized by two ormore, or three or more XRPD signals selected from the group consistingof 19.1°2θ, 25.0°2θ, 5.8°2θ, 10.7°2θ, 22.9°2θ, 18.1°2θ, 24.7 °2θ,11.6°2θ, 21.7°2θ, and 27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate (Form A) is crystalline Tabernanthalog·Sorbate(Form A) characterized by XRPD signals at 19.1°2θ, 25.0°2θ, 5.8°2θ,10.7°2θ, 22.9°2θ, 18.1°2θ, 24.7°2θ, 11.6°2θ, 21.7°2θ, and27.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog·Sorbate (Form A) ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, or nineteen XRPD signals selected from those as set forth inTable 293B.

In some embodiments, the solid form of Tabernanthalog·Sorbate·H₂O iscrystalline Tabernanthalog·Sorbate·H₂O characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.7°2θ, 5.8°2θ, and 17.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·H₂O is crystalline Tabernanthalog·Sorbate·H₂Ocharacterized by XRPD signals at 22.7°2θ, 5.8°2θ, and 17.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·H₂O iscrystalline Tabernanthalog·Sorbate·H₂O characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.7°2θ, 5.8°2θ, 17.0°2θ, 18.7°2θ, and 17.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form ofTabernanthalog·Sorbate·H₂O is crystalline Tabernanthalog·Sorbate·H₂Ocharacterized by XRPD signals at 22.7°2θ, 5.8°2θ, 17.0°2θ, 18.7°2θ, and17.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·H₂O iscrystalline Tabernanthalog·Sorbate·H₂O characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.7°2θ, 5.8°2θ, 17.0°2θ, 18.7°2θ, 17.9°2θ, 30.0°2θ, and 11.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of Tabernanthalog·Sorbate·H₂O is crystallineTabernanthalog·Sorbate·H₂O characterized by XRPD signals at 22.7°2θ,5.8°2θ, 17.0°2θ, 18.7°2θ, 17.9°2θ, 30.0°2θ, and 11.3°2θ (±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of Tabernanthalog·Sorbate·H₂O iscrystalline Tabernanthalog·Sorbate·H₂O characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.7°2θ, 5.8°2θ, 17.0°2θ, 18.7°2θ, 17.9°2θ, 30.0°2θ, 11.3°2θ, 17.4°2θ,18.9°2θ, and 11.7°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).In some embodiments, the solid form of Tabernanthalog·Sorbate·H₂O iscrystalline

Tabernanthalog·Sorbate·H₂O characterized by XRPD signals at 22.7°2θ,5.8°2θ, 17.0°2θ, 18.7°2θ, 17.9°2θ, 30.0°2θ, 11.3°2θ, 17.4°2θ, 18.9°2θ,and 11.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline Tabernanthalog·Sorbate·H₂O ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeenXRPD signals selected from those as set forth in Table 294B.

In one embodiment, the tabernanthalog sorbate salt is characterized byone of the following properties: (1) show minimal reduction in CP (from99.76% area to 99.70% area), (2) is highly soluble in the SIF buffers(apart from FaSSGF), (3) exhibits higher crystallographic quality thanthe tabernanthalog fumarate salt, (4) has better solvent and impurityrejection on scale-up.

In some embodiments, the tabernanthalog sorbate salt (Form I) ischaracterized by at least one of the following properties:

(a) 24.7% w/w th., sorbic acid (i.e., 1.0 mol of API to 1.0 mol sorbicacid);

(b) hydrogen bonding between both oxygen molecules on the sorbate ion.One to N1 (tryptamine nitrogen atom) of one API molecules, the other toN2 (hydro-azepine nitrogen atom) of a separate API molecule. Due tohydrogen bonding present in the structure builds up chains between APIand salt molecule. Causing stacking of API and sorbate molecules closelypacked to one another. This leads to less free space in the crystalstructure and void radius of only ˜0.9 A, much smaller than the 1.4required for a water molecule to occupy. Bond between Sorbates and API,N1-O3, 2.857 Å (hydrogen bond), N2-O2, 2.7015 Å (salification hydrogenbond) N1=Indole, N2=Hydroazepine. Sorbate molecule is disordered andbond lengths stated are an average of the two mapped positions;

(c) Crystal system 100(2) K: monoclinic

-   -   Space group 100(2) K: P2_(1/c)    -   Unit cell 100(2) K: a=9.3410(3)Å, b=6.4173(2)Å, c=30.5108(12) Å.        A=γ=90°β=95.374(3°), V=1820.90(11) Å3    -   Asymmetric unit: contains one API molecule one sorbate ion;

(d) XRPD: 5.7°, 10.5°, 11.4°, 17.9°, 18.8°, 19.1°, 21.4°, 22.6°, 22.9°,24.4°, 24.7°, 26.8° (2θ, 1 d.p) as shown in FIG. 384 and Table 216;

(e) DSC: onset 143.9° C. (−84.1 Jg⁻¹, endotherm, melt) as shown in FIG.453 ;

(f) TGA: onset 171.8° C. (−26.0% w/w, ablation) 250.0° C. (−19.9% w/w,ablation) as shown in FIG. 454 ;

(g) DVS 0 to 90 to 0% RH (dm/dt<0.002%): 0.0 (0.00%), 5.0 (0.0%), 10.0(0.01%), 15.0 (0.01%), 20.0 (0.02%), 25.0 (0.03%), 30.0 (0.03%), 40.0(0.05%), 50.0 (0.07%), 60.0 (0.10%), 70.0 (0.14%), 80.0 (0.21%), 90.0(0.98%), 90.0 (0.98%), 80.0 (0.48%), 70.0 (0.30%), 60.0 (0.18%), 50.0(0.06%), 40.0 (0.03%), 30.0 (0.00%), 25.0 (−0.007%), 20.0 (−0.02%), 15.0(−0.03%), 10.0 (−0.04%), 5.0 (−0.05%), 0.0 (−0.06%) as shown in FIGS.455 and 456 ;

(h) UV chromatographic purity: 99.64% area (212 nm) as shown in FIG. 566.

(i)¹H NMR: (DMSO-d6, 400 MHz); δ 10.4 (s, 1H), 7.2 (d, J=9.4 Hz, 1H),7.1 (dd, J=15.4, 9.6 Hz 1H), 6.7 (d, J=2.3 Hz, 1H), 6.6 (dd, J=8.5, 2.2Hz, 1H), 6.3-6.2 (m, 2H), 5.8 (d, J=15.4 Hz, 1H), 3.7 (s, 3H), 2.9−2.7(m, 8H) 2.4 (s, 3H), 1.8 (d, J=5.9 Hz, 3H) conforms to the molecularstructure (Σ25H*) as shown in FIG. 562 ;

(j) Residual solvents ICH Q3C (R8): 4-A2 (ethanol 0.1% w/w); 3-C1(ethanol 0.3% w/w); 2-V2 (ethanol 0.1% w/w, ICH listed 5000 ppm);

(k) Appearance: columnar, prismatic crystals, [(4-A2), FIGS. 567-572 ];and

(l) Solubility in SIF buffers: Insoluble in FeSSIF at 37° C. up to 1 h.Insoluble in FaSSGF at 37° C. up to 24 h.

In some embodiments, the tabernanthalog sorbate salt (Form A) ischaracterized by at least one of the following properties:

(a) 24.7% w/w th., sorbic acid (i.e., 1.0 mol of API to 1.0 mol sorbicacid);

(b) hydrogen bonding between both oxygen molecules on the sorbate ion.One to N1 (tryptamine nitrogen atom) of one API molecules, the other toN2 (hydro-azepine nitrogen atom) of a separate API molecule. Due tohydrogen bonding present in the structure builds up chains between APIand salt molecule. Causing stacking of API and sorbate molecules closelypacked to one another. This leads to less free space in the crystalstructure and void radius of only ˜0.9 A, much smaller than the 1.4required for a water molecule to occupy. Bond between Sorbates and API,N1-O3, 2.857 Å (hydrogen bond), N2-O2, 2.7015 Å (salification hydrogenbond) N1=Indole, N2=Hydroazepine. Sorbate molecule is disordered andbond lengths stated are an average of the two mapped positions;

(c) Crystal system 100(2) K: monoclinic

-   -   Space group 100(2) K: P2_(1/c)    -   Unit cell 100(2) K: a=9.3410(3)Å, b=6.4173(2)Å, c=30.5108(12) Å.        A=γ=90°β=95.374(3)°, V=1820.90(11) Å^(3.)    -   Asymmetric unit: contains one API molecule one sorbate ion;

(d) XRPD: 5.7°, 11.4°, 22.8° as shown in FIG. 564 and Table 273;

(e) DSC: onset 140.03° C. (−106.66 Jg⁻¹, endotherm, melt);

(f) TGA: onset 177.6° C. (−36.4% w/w, ablation) 263.5° C. (−59% w/w,ablation); (g) DVS 0 to 90 to 0% RH (dm/dt<0.002%): 0.0 (0.00%), 5.0(0.0%), 10.0 (0.01%), 15.0 (0.01%), 20.0 (0.02%), 25.0 (0.03%), 30.0(0.03%), 40.0 (0.05%), 50.0 (0.07%), 60.0 (0.10%), 70.0 (0.14%), 80.0(0.21%), 90.0 (0.98%), 90.0 (0.98%), 80.0 (0.48%), 70.0 (0.30%), 60.0(0.18%), 50.0 (0.06%), 40.0 (0.03%), 30.0 (0.00%), 25.0 (0.00%), 20.0(0.02%), 15.0 (0.03%), 10.0 (0.04%), 5.0 (0.05%), 0.0 (0.06%);

(h) UV chromatographic purity: 99.64% area (212 nm);

(i)¹H NMR: (DMSO-d₆, 40° MHz); δ 10.5 (s, 1H), 7.2 (d, J=8.56 Hz, 1H),7.1 (dd, J=15.2, 15.3 Hz, 1H), 6.7 (d, J=1.9 Hz, 1H), 6.6 (dd, J=8.56,2.2 Hz, 1H), 6.2 (d, m, 2H), 5.8 (d, J=15.0 Hz, 1H), 3.7 (s, 3H), 2.8(m, 2H), 2.7 (m, 6H), 2.4 (s, 3H), 1.8 (d, J=5.8 Hz, 3H) ppm; conformsto the molecular structure (Σ25H) as shown FIG. 564 ;

(j) Residual solvents ICH Q3C (R8): ethanol 0.1% w/w, ICH listed 5000ppm; and

(k) Q ¹H NMR: 99.9% w/w.

In some embodiments, the tabernanthalog sorbate salt (Form A) has acrystal data when collected using Single Crystal XRD as follows:C₂₀H₂₆N20₃, M_(r)=342.43, monoclinic, P2_(1/c) (No. 14), a=9.3410(3)Å,b=6.4173(2)Å, c=30.5108(12)Å, b=95.374(3)°, a=g=900, V=1820.90(11) Å³,T=100(2) K, Z=4, Z′=1, m(Cu Kα)=0.675 mm⁻¹, 13832 reflections measured,3694 unique (R_(int)=0.0462) which were used in all calculations. Thefinal wR₂ was 0.2098 (all data) and R_(I) was 0.0826 (I≥2σ(I)).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by XRPD signals at 5.7°2θ,11.4°2θ, and 22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by two or more, or three XRPDsignals selected from the group consisting of 5.7°2θ, 11.4°2θ, and22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by XRPD signals at 5.7°2θ,11.4°2θ, 22.6°2θ and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form A) and characterized by two or more, or three XRPDsignals selected from the group consisting of 5.7°2θ, 11.4°2θ, 22.6°2θand 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt (Form B, Pattern#1) is characterized by at least one of the following properties:

(a) XRPD: 7.5°, 15.1°;

(b) DSC: onset 48.4° C. (−231.36 Jg⁻¹, endotherm, dehydration), 69.9° C.(−160.38 Jg⁻¹, endotherm, dehydration), 144.6° C. (−102.24 Jg⁻¹,endotherm, melt);

(c) TGA: onset 54.8° C. (−1.37% w/w, dehydration; this event wasobserved when sample was re-prepared for TGA analysis after 7 days(refer to FIG. 564 ) 164.37° C. (−29.24% w/w, ablation); and

(d)¹H NMR: (DMSO-d₆, 40° MHz); δ 10.3 (s, 1H), 7.2 (d, J=8.56 Hz, 1H),7.1 (ddd, J=15.2, 15.3, 0.56 Hz, 1H), 6.7 (d, J=2.24 Hz, 1H), 6.6 (dd,J=8.54, 2.33 Hz, 1H), 6.2 (d, m, 2H), 5.8 (d, J=15.32 Hz, 1H), 3.7 (s,3H), 2.8 (m, 2H), 2.7 (m, 6H), 2.4 (s, 3H), 1.8 (d, J=5.96 Hz, 3H) ppm;conforms to the molecular structure (Σ25H).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form B; Pattern #1) and characterized by XRPD signals at7.5°2θ, and 15.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt (Form C, Pattern#2) is characterized by at least one of the following properties:

(a) XRPD: 5.7° 11.1°, 11.5°, 13.9°, 16.7°, 17.3°, 17.8°, 18.5°, 18.7°,20.1°, 22.4°, 29.7°; (b) DSC: onset 76.6° C. (−99.32 Jg⁻¹, endotherm),145.1° C. (−95.88 Jg⁻¹, endotherm); (c) TGA: onset 71.6° C. (−4.4% w/w,dehydration), 168.7° C. (−27.9% w/w, ablation); (d) UV chromatographicpurity: 99.69% area (212 nm); and

(e)¹H NMR: (DMSO-d₆, 40° MHz); δ 10.3 (s, 1H), 7.2 (d, J=8.6 Hz, 1H),7.1 (ddd, J=15.3, 14.8, 0.56 Hz, 1H), 6.7 (d, J=2.2 Hz, 1H), 6.6 (dd,J=10.8, 6.2 Hz, 1H), 6.2 (m, 2H), 5.8 (d, J=15.3 Hz, 1H), 3.7 (s, 3H),2.9 (m, 2H), 2.7 (m, 6H), 2.4 (s, 3H), 1.8 (d, J=5.9 Hz, 3H) ppm;conforms to the molecular structure (Σ25H).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form C; Pattern #2) and characterized by XRPD signals at5.7°2θ, and 11.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form C; Pattern #2) and characterized by XRPD signals at5.7°2θ, 22.4°2θ, 11.5°2θ, 16.7°2θ, 17.3°2θ, 18.5°2θ, 18.7°2θ, 17.8°2θ,11.2°2θ, 20.1°2θ, 13.9°2θ, and 29.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the tabernanthalog sorbate salt is crystallinepolymorphic (Form C; Pattern #2) and characterized by two or more, orthree XRPD signals selected from the group consisting of 5.7°2θ,22.4°2θ, 11.5°2θ, 16.7°2θ, 17.3°2θ, 18.5°2θ, 18.7°2θ, 17.8°2θ, 11.2°2θ,20.1°2θ, 13.9°2θ, and 29.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the tabernanthalog sorbate salt·H₂O (hydrate) has acrystal data when collected using Single Crystal XRD as follows:C₂₀H₂₈N20₄, M_(r)=360.44, monoclinic, P2_(1/c) (No. 14),a=16.07470(10)Å, b=12.14150(10)Å, c=10.85080(10)Å, b=109.2390(10°),a=g=90°, V=1999.49(3) Å³, T=100(2) K, Z=4, Z′=1, m(Cu Kα)=0.676 mm¹,51305 reflections measured, 3786 unique (R_(int)=0.0483) which were usedin all calculations. The final wR₂ was 0.0874 (all data) and R_(I) was0.0347 (I≥2σ(I)).

Tabernanthalog Tartrate Salt

In yet other embodiments, the tabernanthalog tartrate salt is obtainedfrom heat-up/cool-down crystallization of tabernanthalog (native) withL-tartaric acid in ethanol (11.2 vol) and water (7.2 vol) at 85° C. Theproduct was isolated by centrifugation and was oven-dried under reducedpressure over 20 h at 40° C.

In yet other embodiments, the tabernanthalog tartrate salt is obtainedfrom heat-up/cool-down crystallization of tabernanthalog (native) withL-tartaric acid in ethanol (5.0 vol) and water (5.75 vol) at 85° C.Product was isolated by filtration and dried under sustained nitrogenflux (<1 bar) over 20 h at 20° C.

In one embodiment, the tabernanthalog tartrate salt is crystallinecharacterized by two or more, or three XRPD signals selected from thegroup consisting of 17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ, 16.4°2θ,28.3°2θ, 19.9°2θ, and 24°2θ, 26.1°2θ, 16.1°2θ, 37.8°2θ, 24.3°2θ,34.3°2θ, 32.9°2θ, 38.1°2θ, 26.8°2θ, 32.6°2θ, and 18.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, the tabernanthalog tartrate salt is crystallinecharacterized by two or more, or three XRPD signals selected from thegroup consisting of 17.3°2θ, 20.4°2θ, and 21.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In one embodiment, the tabernanthalog tartrate salt is crystallinecharacterized by XRPD signals at 17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ,16.4°2θ, 28.3°2θ, 19.9°2θ, and 24°2θ, 26.1°2θ, 16.1°2θ, 37.8°2θ,24.3°2θ, 34.3°2θ, 32.9°2θ, 38.1°2θ, 26.8°2θ, 32.6°2θ, and18.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, the tabernanthalog tartrate salt is crystallinecharacterized by XRPD signals at 17.3°2θ, 20.4°2θ, and 21.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog tartrate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 217.

In some embodiments, the tabernanthalog tartrate salt is crystallinecharacterized two or more, or three XRPD signals as shown in FIG. 385 .

In some embodiments, Form A of the tabernanthalog tartrate salt exhibitsan XRPD pattern post DVS as depicted in FIG. 474 .

In some embodiments the tabernanthalog tartrate salt exhibits an ¹H NMRspectrum as depicted in FIG. 467 , FIG. 545 , or FIG. 546 .

In some embodiments the tabernanthalog tartrate salt is a unary tartratewith 39.5% w/w th., L-tartaric acid (i.e., 1.0 mol of API to 1.0 molfumaric acid).

In some embodiments, the tabernanthalog tartrate salt exhibits a DSCprofile as depicted in FIG. 469 .

In some embodiments, the tabernanthalog tartrate salt exhibits a TGAprofile as depicted in FIG. 470 .

In some embodiments, the tabernanthalog tartrate salt exhibits a DVSprofile as depicted in FIG. 471 or FIG. 472 .

In some embodiments, the tabernanthalog tartrate salt exhibits an HPLCspectrum as depicted in FIG. 476 .

In some embodiments, the tabernanthalog tartrate salt exhibits at leastone property as listed in Table 193.

Tabernanthalog Benzoate Salt

In yet other embodiments, the tabernanthalog benzoate salt is obtainedfrom heat-up/cool-down crystallization of tabernanthalog (native) withbenzoic acid in ethanol (8.4 vol) and water (1.4 vol) at 85° C. Theproduct was isolated by centrifugation and was oven-dried under reducedpressure over 20 h at 40° C.

In yet other embodiments, the tabernanthalog benzoate salt is obtainedfrom heat-up/cool-down crystallization of tabernanthalog (native) withbenzoic acid in ethanol (5.0 vol) and water (0.85 vol) at 85° C. Productwas isolated by filtration and dried under sustained nitrogen flux (<1bar) over 20 h at 20° C.

In one embodiment, the tabernanthalog benzoate salt is crystallinecharacterized by two or more, or three XRPD signals selected from thegroup consisting of 9°2θ, 18.1°2θ, 23.7°2θ, 26.3°2θ, 16.7°2θ, 28.9°2θ,15.6°2θ, and 17.7°2θ, 19.6°2θ, 22.9°2θ, 24.4°2θ, 21.3°2θ, and14.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, the tabernanthalog benzoate salt is crystallinecharacterized by two or more, or three XRPD signals selected from thegroup consisting of 9°2θ, 18.1°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In one embodiment, the tabernanthalog benzoate salt is crystallinecharacterized by signals at 9°2θ, 18.1°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ;or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, the tabernanthalog benzoate salt is crystallinecharacterized by XRPD signals at 9°2θ, 18.1°2θ, 23.7°2θ, 26.3°2θ,16.7°2θ, 28.9°2θ, 15.6°2θ, 17.7°2θ, 19.6°2θ, and 22.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In one embodiment, the tabernanthalog benzoate salt is crystallinecharacterized by XRPD signals at 9°2θ, 18.1°2θ, and 23.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the tabernanthalog benzoate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 218.

In some embodiments, the tabernanthalog benzoate salt is crystallinecharacterized two or more, or three XRPD signals as shown in FIG. 388 .

In some embodiments, Form A of the tabernanthalog benzoate salt exhibitsan XRPD pattern post DVS as depicted in FIG. 486(C).

In some embodiments the tabernanthalog benzoate salt exhibits an ¹H NMRspectrum as depicted in FIG. 493 , FIG. 547 , or FIG. 548 .

In some embodiments the tabernanthalog benzoate salt is a unary benzoatewith 34.6% w/w th., benzoic acid (i.e., 1.0 mol of API to 1.0 molbenzoic acid).

In some embodiments, the tabernanthalog benzoate salt exhibits a DSCprofile as depicted in FIG. 495 or FIG. 552 .

In some embodiments, the tabernanthalog benzoate salt exhibits a TGAprofile as depicted in FIG. 496 or FIG. 556 .

In some embodiments, the tabernanthalog benzoate salt exhibits a DVSprofile as depicted in FIG. 486(A) or FIG. 486(B).

In some embodiments, the tabernanthalog benzoate salt exhibits an HPLCspectrum as depicted in FIG. 486(E).

In some embodiments, the tabernanthalog benzoate salt exhibits at leastone property as listed in Table 194.

Other Tabernanthalog Salts and Other Embodiments

In some embodiments, the tabernanthalog malate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 219.

In some embodiments, the tabernanthalog tosylate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 220.

In some embodiments, the tabernanthalog adipate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 221.

In some embodiments, the tabernanthalog glucuronate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 222.

In some embodiments, the tabernanthalog phosphate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 223.

In some embodiments, the tabernanthalog edisylate salt is crystallinecharacterized two or more, or three XRPD signals as shown in Table 224.

In some embodiments, the solid form of native tabernanthalog iscrystalline native tabernanthalog characterized by two or more, or threeor more XRPD signals selected from the group consisting of 18.9°2θ,27.3°2θ, and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of native tabernanthalog is crystallinenative tabernanthalog characterized by XRPD signals 18.9°2θ, 27.3°2θ,and 27.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of native tabernanthalog iscrystalline native tabernanthalog characterized by two or more, or threeor more XRPD signals selected from the group consisting of 18.9°2θ,27.3°2θ, 27.4°2θ, 15.1°2θ, and 10.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation). In some embodiments, the solid form of nativetabernanthalog is crystalline native tabernanthalog characterized byXRPD signals at 18.9°2θ, 27.3°2θ, 27.4°2θ, 15.1°2θ, and 10.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline native tabernanthalog ischaracterized by one, two, three, four, or five XRPD signals selectedfrom those set forth in Table 215.

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by XRPD signals at5.7°2θ, 11.4°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, and 10.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate salt is crystalline tabernanthalog sorbatecharacterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, and10.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ, 22.6°2θ, and 24.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog sorbate salt is crystalline tabernanthalogsorbate characterized by XRPD signals at 5.7°2θ, 11.4°2θ, 24.7°2θ,18.8°2θ, 10.5°2θ, 22.6°2θ, and 24.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ, 19.1°2θ,and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by XRPD signals at5.7°2θ, 11.4°2θ, 24.7°2θ, 18.8°2θ, 10.5°2θ, 22.6°2θ, 24.4°2θ, 26.9°2θ,19.1°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, or twelve XRPD signals selected from those set forth inTable 216.

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, and 21.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog tartratesalt is crystalline tabernanthalog tartrate characterized by XRPDsignals at 17.3°2θ, 20.4°2θ, and 21.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog tartrate salt is crystalline tabernanthalog tartratecharacterized by XRPD signals at 17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ, and16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ, 16.4°2θ, 28.3°2θ, and19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ, 16.4°2θ, 28.3°2θ, and19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ, 16.4°2θ, 28.3°2θ, 19.9°2θ, 24.0 °2θ,26.1°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.3°2θ, 20.4°2θ, 21.3°2θ, 22.4°2θ, 16.4°2θ, 28.3°2θ, 19.9°2θ, 24.0°2θ,26.1°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog tartrate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, oreighteen XRPD signals selected from those set forth in Table 217.

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 9.0°2θ,18.1°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by XRPD signals at9.0°2θ, 18.1°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at9.0°2θ, 18.1°2θ, 23.7°2θ, 26.3°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate salt is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 9.0°2θ, 18.1°2θ, 23.7°2θ, 26.3°2θ, and16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 9.0°2θ,18.1°2θ, 23.7°2θ, 26.3°2θ, 16.7°2θ, 28.9°2θ, and 15.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog benzoate salt is crystalline tabernanthalogbenzoate characterized by XRPD signals at 9.0°2θ, 18.1°2θ, 23.7°2θ,26.3°2θ, 16.7°2θ, 28.9°2θ, and 15.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 9.0°2θ,18.1°2θ, 23.7°2θ, 26.3°2θ, 16.7°2θ, 28.9°2θ, 15.6°2θ, 17.7°2θ, 19.6°2θ,and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by XRPD signals at9.0°2θ, 18.1°2θ, 23.7°2θ, 26.3°2θ, 16.7°2θ, 28.9°2θ, 15.6°2θ, 17.7°2θ,19.6°2θ, and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, or thirteen XRPD signals selected from those setforth in Table 218.

In some embodiments, the solid form of tabernanthalog malate salt iscrystalline tabernanthalog malate characterized by two or more, or threeor more XRPD signals selected from the group consisting of 19.5°2θ,21.4°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form tabernanthalog malate salt iscrystalline tabernanthalog malate characterized by XRPD signals at19.5°2θ, 21.4°2θ, and 16.7°2θ, (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog malate salt iscrystalline tabernanthalog malate characterized by two or more, or threeor more XRPD signals selected from the group consisting of at 19.5°2θ,21.4°2θ, 16.7°2θ, 14.0°2θ, and 27.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogmalate salt is crystalline tabernanthalog malate characterized by XRPDsignals at 19.5°2θ, 21.4°2θ, 16.7°2θ, 14.0°2θ, and 27.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog malate salt iscrystalline tabernanthalog malate characterized by two or more, or threeor more XRPD signals selected from the group consisting of 19.5°2θ,21.4°2θ, 16.7°2θ, 14.0°2θ, 27.0°2θ, 18.3°2θ, and 25.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog malate salt is crystalline tabernanthalog malatecharacterized by XRPD signals at 19.5°2θ, 21.4°2θ, 16.7°2θ, 14.0°2θ,27.0°2θ, 18.3°2θ, and 25.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog malate salt iscrystalline tabernanthalog malate characterized by two or more, or threeor more XRPD signals selected from the group consisting of 19.5°2θ,21.4°2θ, 16.7°2θ, 14.0°2θ, 27.0°2θ, 18.3°2θ, 25.1°2θ, 23.9°2θ, 31.2°2θand 6.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog malate salt is crystallinetabernanthalog malate characterized by XRPD signals at 19.5°2θ, 21.4°2θ,16.7°2θ, 14.0°2θ, 27.0°2θ, 18.3°2θ, 25.1°2θ, 23.9°2θ, 31.2°2θ and6.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog malate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, or thirteen XRPD signals selected from those setforth in Table 219.

In some embodiments, the solid form of tabernanthalog tosylate salt iscrystalline tabernanthalog tosylate characterized by one or two XRPDsignals selected from the group consisting of 5.5°2θ and11.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form tabernanthalog tosylate salt is crystallinetabernanthalog tosylate characterized by XRPD signals at 5.5°2θ and11.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog tosylate salt ischaracterized by one, or two XRPD signals selected from those set forthin Table 220.

In some embodiments, the solid form of tabernanthalog adipate salt iscrystalline tabernanthalog adipate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.8°2θ, 20.6°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog adipatesalt is crystalline tabernanthalog adipate characterized by XRPD signalsat 17.8°2θ, 20.6°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog adipate salt iscrystalline tabernanthalog adipate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at17.8°2θ, 20.6°2θ, 19.4°2θ, 15.7°2θ, and 21.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog adipate salt is crystalline tabernanthalog adipatecharacterized by XRPD signals at 17.8°2θ, 20.6°2θ, 19.4°2θ, 15.7°2θ, and21.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog adipate salt iscrystalline tabernanthalog adipate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.8°2θ, 20.6°2θ, 19.4°2θ, 15.7°2θ, 21.0°2θ, 16.5°2θ, and24.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog adipate salt iscrystalline tabernanthalog adipate characterized by XRPD signals at17.8°2θ, 20.6°2θ, 19.4°2θ, 15.7°2θ, 21.0°2θ, 16.5°2θ, and24.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog adipate salt iscrystalline tabernanthalog adipate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.8°2θ, 20.6°2θ, 19.4°2θ, 15.7°2θ, 21.0°2θ, 16.5°2θ, 24.0°2θ, 25.5°2θ,21.8°2θ, and 18.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog adipate salt iscrystalline tabernanthalog adipate characterized by XRPD signals at17.8°2θ, 20.6°2θ, 19.4°2θ, 15.7°2θ, 21.0°2θ, 16.5°2θ, 24.0 °2θ, 25.5°2θ,21.8°2θ, and 18.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog adipate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeenXRPD signals selected from those set forth in Table 221.

In some embodiments, the solid form of tabernanthalog glucoronate saltis crystalline tabernanthalog glucoronate characterized by two or more,or three or more XRPD signals selected from the group consisting of20.7°2θ, 20.1°2θ, and 6.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalogglucoronate salt is crystalline tabernanthalog glucoronate characterizedby XRPD signals at 20.7°2θ, 20.1°2θ, and 6.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog glucoronate saltis crystalline tabernanthalog glucoronate characterized by two or more,or three or more XRPD signals selected from the group consisting of at20.7°2θ, 20.1°2θ, 6.6°2θ, 12.5°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog glucoronate salt is crystalline tabernanthalogglucoronate characterized by XRPD signals at 20.7°2θ, 20.1°2θ, 6.6°2θ,12.5°2θ, and 18.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog glucoronate saltis crystalline tabernanthalog glucoronate characterized by two or more,or three or more XRPD signals selected from the group consisting of20.7°2θ, 20.1°2θ, 6.6°2θ, 12.5°2θ, 18.1°2θ, 24.5°2θ, and22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog glucoronate salt iscrystalline tabernanthalog glucoronate characterized by XRPD signals at20.7°2θ, 20.1°2θ, 6.6°2θ, 12.5°2θ, 18.1°2θ, 24.5°2θ, and22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog glucoronate saltis crystalline tabernanthalog glucoronate characterized by two or more,or three or more XRPD signals selected from the group consisting of20.7°2θ, 20.1°2θ, 6.6°2θ, 12.5°2θ, 18.1°2θ, 24.5°2θ, 22.9°2θ, 18.7°2θ,15.1°2θ, and 29.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog glucoronate salt iscrystalline tabernanthalog glucoronate characterized by XRPD signals at20.7°2θ, 20.1°2θ, 6.6°2θ, 12.5°2θ, 18.1°2θ, 24.5°2θ, 22.9°2θ, 18.7°2θ,15.1°2θ, and 29.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog glucoronate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three,twenty-four, twenty-five, twenty-six, twenty-seven XRPD signals selectedfrom those set forth in Table 222.

In some embodiments, the solid form of tabernanthalog phosphate salt iscrystalline tabernanthalog phosphate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.3°2θ,14.4°2θ, and 14.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form tabernanthalog phosphate salt iscrystalline tabernanthalog phosphate characterized by XRPD signals at5.3°2θ, 14.4°2θ, and 14.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog phosphate salt iscrystalline tabernanthalog phosphate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at5.3°2θ, 14.4°2θ, 14.7°2θ, 20.2°2θ, and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog phosphate salt is crystalline tabernanthalog phosphatecharacterized by XRPD signals at 5.3°2θ, 14.4°2θ, 14.7°2θ, 20.2°2θ, and22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog phosphate salt iscrystalline tabernanthalog phosphate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.3°2θ,14.4°2θ, 14.7°2θ, 20.2°2θ, 22.9°2θ, 24.0°2θ, and 22.7°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog phosphate salt is crystalline tabernanthalogphosphate characterized by XRPD signals at 5.3°2θ, 14.4°2θ, 14.7°2θ,20.2°2θ, 22.9°2θ, 24.0°2θ, and 22.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog phosphate salt iscrystalline tabernanthalog phosphate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.3°2θ,14.4°2θ, 14.7°2θ, 20.2°2θ, 22.9°2θ, 24.0°2θ, 22.7°2θ, 25.5°2θ, 19.7°2θ,and 24.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog phosphate salt iscrystalline tabernanthalog phosphate characterized by XRPD signals at5.3°2θ, 14.4°2θ, 14.7°2θ, 20.2°2θ, 22.9°2θ, 24.0 °2θ, 22.7°2θ, 25.5°2θ,19.7°2θ, and 24.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog phosphate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, or twenty XRPD signals selected from those set forthin Table 223.

In some embodiments, the solid form of tabernanthalog edisylate salt iscrystalline tabernanthalog edisylate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.4°2θ, 19.9°2θ, and 20.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog edisylatesalt is crystalline tabernanthalog edisylate characterized by XRPDsignals at 17.4°2θ, 19.9°2θ, and 20.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog edisylate salt iscrystalline tabernanthalog edisylate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at17.4°2θ, 19.9°2θ, 20.8°2θ, 21.8°2θ, and 12.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog edisylate salt is crystalline tabernanthalog edisylatecharacterized by XRPD signals at 17.4°2θ, 19.9°2θ, 20.8°2θ, 21.8°2θ, and12.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog edisylate salt iscrystalline tabernanthalog edisylate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.4°2θ, 19.9°2θ, 20.8°2θ, 21.8°2θ, 12.6°2θ, 20.4°2θ, and12.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog edisylate salt iscrystalline tabernanthalog edisylate characterized by XRPD signals at17.4°2θ, 19.9°2θ, 20.8°2θ, 21.8°2θ, 12.6°2θ, 20.4°2θ, and12.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog edisylate salt iscrystalline tabernanthalog edisylate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.4°2θ, 19.9°2θ, 20.8°2θ, 21.8°2θ, 12.6°2θ, 20.4°2θ, 12.8°2θ, 18.4°2θ,4.5°2θ, and 19.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog edisylate salt iscrystalline tabernanthalog edisylate characterized by XRPD signals at17.4°2θ, 19.9°2θ, 20.8°2θ, 21.8°2θ, 12.6°2θ, 20.4°2θ, 12.8°2θ, 18.4°2θ,4.5°2θ, and 19.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog edisylate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three,twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight,twenty-nine, thirty, thirty-one, thirty-two XRPD signals selected fromthose set forth in Table 224.

In some embodiments, the solid form of tabernanthalog maleate salt iscrystalline tabernanthalog maleate characterized by two or more, orthree or more XRPD signals selected from the group consisting of20.7°2θ, 26.8°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog maleatesalt is crystalline tabernanthalog maleate characterized by XRPD signalsat 20.7°2θ, 26.8°2θ, and 19.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog maleate salt iscrystalline tabernanthalog maleate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at20.7°2θ, 26.8°2θ, 19.4°2θ, 25.3°2θ, and 12.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog maleate salt is crystalline tabernanthalog maleatecharacterized by XRPD signals at 20.7°2θ, 26.8°2θ, 19.4°2θ, 25.3°2θ, and12.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog maleate salt iscrystalline tabernanthalog maleate characterized by two or more, orthree or more XRPD signals selected from the group consisting of20.7°2θ, 26.8°2θ, 19.4°2θ, 25.3°2θ, 12.6°2θ, 22.2°2θ, and10.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog maleate salt iscrystalline tabernanthalog maleate characterized by XRPD signals at20.7°2θ, 26.8°2θ, 19.4°2θ, 25.3°2θ, 12.6°2θ, 22.2°2θ, and10.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog maleate salt iscrystalline tabernanthalog maleate characterized by two or more, orthree or more XRPD signals selected from the group consisting of20.7°2θ, 26.8°2θ, 19.4°2θ, 25.3°2θ, 12.6°2θ, 22.2°2θ, 10.4°2θ, 18.9°2θ,25.3°2θ, and 21.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog maleate salt iscrystalline tabernanthalog maleate characterized by XRPD signals at20.7°2θ, 26.8°2θ, 19.4°2θ, 25.3°2θ, 12.6°2θ, 22.2°2θ, 10.4°2θ, 18.9°2θ,25.3°2θ, and 21.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog maleate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signalsselected from those set forth in Table 225.

In some embodiments, the solid form of tabernanthalog galactarate saltis crystalline tabernanthalog galactarate characterized by two or more,or three or more XRPD signals selected from the group consisting of19.6°2θ, 30.7°2θ, and 37.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthaloggalactarate salt is crystalline tabernanthalog galactarate characterizedby XRPD signals at 19.6°2θ, 30.7°2θ, and 37.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog galactarate saltis crystalline tabernanthalog galactarate characterized by two or more,or three or more XRPD signals selected from the group consisting of at19.6°2θ, 30.7°2θ, 37.7°2θ, 18.1°2θ, and 37.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog galactarate salt is crystalline tabernanthaloggalactarate characterized by XRPD signals at 19.6°2θ, 30.7°2θ, 37.7°2θ,18.1°2θ, and 37.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog galactarate saltis crystalline tabernanthalog galactarate characterized by two or more,or three or more XRPD signals selected from the group consisting of19.6°2θ, 30.7°2θ, 37.7°2θ, 18.1°2θ, 37.6°2θ, 5.7°2θ, and34.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog galactarate salt iscrystalline tabernanthalog galactarate characterized by XRPD signals at19.6°2θ, 30.7°2θ, 37.7°2θ, 18.1°2θ, 37.6°2θ, 5.7°2θ, and34.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog galactarate saltis crystalline tabernanthalog galactarate characterized by two or more,or three or more XRPD signals selected from the group consisting of19.6°2θ, 30.7°2θ, 37.7°2θ, 18.1°2θ, 37.6°2θ, 5.7°2θ, 34.5°2θ, 21.5°2θ,26.8°2θ, and 36.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog galactarate salt iscrystalline tabernanthalog galactarate characterized by XRPD signals at19.6°2θ, 30.7°2θ, 37.7°2θ, 18.1°2θ, 37.6°2θ, 5.7°2θ, 34.5°2θ, 21.5°2θ,26.8°2θ, and 36.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the crystalline tabernanthalog galactarate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen,eighteen, nineteen, or twenty XRPD signals selected from those set forthin Table 226.

In some embodiments, the solid form of tabernanthalog citrate salt iscrystalline tabernanthalog citrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of16.6°2θ, 12.5°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog citratesalt is crystalline tabernanthalog citrate characterized by XRPD signalsat 16.6°2θ, 12.5°2θ, and 20.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog citrate salt iscrystalline tabernanthalog citrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at16.6°2θ, 12.5°2θ, 20.9°2θ, 13.0°2θ, and 21.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog citrate salt is crystalline tabernanthalog citratecharacterized by XRPD signals at 16.6°2θ, 12.5°2θ, 20.9°2θ, 13.0°2θ, and21.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog citrate salt iscrystalline tabernanthalog citrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of16.6°2θ, 12.5°2θ, 20.9°2θ, 13.0°2θ, 21.9°2θ, 23.7°2θ, and17.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog citrate salt iscrystalline tabernanthalog citrate characterized by XRPD signals at16.6°2θ, 12.5°2θ, 20.9°2θ, 13.0°2θ, 21.9°2θ, 23.7°2θ, and17.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog citrate salt iscrystalline tabernanthalog citrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of16.6°2θ, 12.5°2θ, 20.9°2θ, 13.0°2θ, 21.9°2θ, 23.7°2θ, 17.6°2θ, 17.7°2θ,26.0°2θ, and 19.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog citrate salt iscrystalline tabernanthalog citrate characterized by XRPD signals at16.6°2θ, 12.5°2θ, 20.9°2θ, 13.0°2θ, 21.9°2θ, 23.7°2θ, 17.6°2θ, 17.7°2θ,26.0°2θ, and 19.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog citrate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, or thirteen XRPD signals selected from those setforth in Table 227.

In some embodiments, the solid form of tabernanthalog glycolate salt iscrystalline tabernanthalog glycolate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.5°2θ, 18.0°2θ, and 23.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog glycolatesalt is crystalline tabernanthalog glycolate characterized by XRPDsignals at 23.5°2θ, 18.0°2θ, and 23.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog glycolate salt iscrystalline tabernanthalog glycolate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at23.5°2θ, 18.0°2θ, 23.4°2θ, 9.1°2θ, and 9.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog glycolate salt is crystalline tabernanthalog glycolatecharacterized by XRPD signals at 23.5°2θ, 18.0°2θ, 23.4°2θ, 9.1°2θ, and9.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog glycolate salt iscrystalline tabernanthalog glycolate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.5°2θ, 18.0°2θ, 23.4°2θ, 9.1°2θ, 9.7°2θ, 19.0°2θ, and 18.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog glycolate salt is crystalline tabernanthalogglycolate characterized by XRPD signals at 23.5°2θ, 18.0°2θ, 23.4°2θ,9.1°2θ, 9.7°2θ, 19.0°2θ, and 18.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog glycolate salt iscrystalline tabernanthalog glycolate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.5°2θ, 18.0°2θ, 23.4°2θ, 9.1°2θ, 9.7°2θ, 19.0°2θ, 18.3°2θ, 19.6°2θ,19.8°2θ, and 29.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog glycolate salt iscrystalline tabernanthalog glycolate characterized by XRPD signals at23.5°2θ, 18.0°2θ, 23.4°2θ, 9.1°2θ, 9.7°2θ, 19.0°2θ, 18.3°2θ, 19.6°2θ,19.8°2θ, and 29.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the crystalline tabernanthalog glycolate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPDsignals selected from those set forth in Table 228.

In some embodiments, the solid form of tabernanthalog succinate salt iscrystalline tabernanthalog succinate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.3°2θ,17.2°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form tabernanthalog succinate salt iscrystalline tabernanthalog succinate characterized by XRPD signals at8.3°2θ, 17.2°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog succinate salt iscrystalline tabernanthalog succinate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at8.3°2θ, 17.2°2θ, 24.7°2θ, 22.2°2θ, and 15.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog succinate salt is crystalline tabernanthalog succinatecharacterized by XRPD signals 8.3°2θ, 17.2°2θ, 24.7°2θ, 22.2°2θ, and15.4 (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog succinate salt iscrystalline tabernanthalog succinate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.3°2θ,17.2°2θ, 24.7°2θ, 22.2°2θ, 15.4°2θ, 24.1°2θ, and 16.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog succinate salt is crystalline tabernanthalogsuccinate characterized by XRPD signals at 8.3°2θ, 17.2°2θ, 24.7°2θ,22.2°2θ, 15.4°2θ, 24.1°2θ, and 16.1 (±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog succinate salt iscrystalline tabernanthalog succinate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.3°2θ,17.2°2θ, 24.7°2θ, 22.2°2θ, 15.4°2θ, 24.1°2θ, 16.1°2θ, 11.0°2θ, 21.3°2θ,and 20.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog succinate salt iscrystalline tabernanthalog succinate characterized by XRPD signals at8.3°2θ, 17.2°2θ, 24.7°2θ, 22.2°2θ, 15.4°2θ, 24.1°2θ, 16.1°2θ, 11.0°2θ,21.3°2θ, and 20.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog succinate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeenXRPD signals selected from those set forth in Table 229.

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog tartratesalt is crystalline tabernanthalog tartrate characterized by XRPDsignals at 17.3°2θ, 20.4°2θ, and 22.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of at17.3°2θ, 20.4°2θ, 22.3°2θ, 21.3°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog tartrate salt is crystalline tabernanthalog tartratecharacterized by XRPD signals 17.3°2θ, 20.4°2θ, 22.3°2θ, 21.3°2θ, and16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, 22.3°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, and19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.3°2θ, 20.4°2θ, 22.3°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, and19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, 22.3°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, 19.9°2θ, 26.1°2θ,24.0°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog tartrate salt iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.3°2θ, 20.4°2θ, 22.3°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, 19.9°2θ, 26.1°2θ,24.0°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog tartrate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signalsselected from those set forth in Table 230.

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more XRPDsignals selected from the group consisting of 9.0°2θ, 18.0°2θ, and23.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by XRPD signals at9.0°2θ, 18.0°2θ, and 23.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog benzoate salt ischaracterized by one, two, or three XRPD signals selected from those setforth in Table 231.

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by two or more XRPDsignals selected from the group consisting of 5.7°2θ, 11.4°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by XRPD signals at5.7°2θ, 11.4°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by two, three, or moreXRPD signals selected from the group consisting of 5.7°2θ, 11.4°2θ,24.7°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by XRPD signals at5.7°2θ, 11.4°2θ, 24.7°2θ, and 22.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, three, or four XRPD signals selected fromthose set forth in Table 232.

In some embodiments, the solid form of tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by two or more XRPDsignals selected from the group consisting of 5.7°2θ, 11.4°2θ, and22.8°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form tabernanthalog sorbate salt iscrystalline tabernanthalog sorbate characterized by XRPD signals at5.7°2θ, 11.4°2θ, and 22.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog sorbate salt ischaracterized by one, two, or three XRPD signals selected from those setforth in Table 233.

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog benzoatesalt is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 9.0°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate salt is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 18.1°2θ, 16.7°2θ, 9.0°2θ, and15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, and14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.7°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, and14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, 14.2°2θ, 23.0 °2θ,21.4°2θ and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.7°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, 14.2°2θ, 23.0°2θ,21.4°2θ and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPDsignals selected from those set forth in Table 234.

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form tabernanthalog benzoatesalt is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 18.1°2θ, and 16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.8°2θ, 9.0°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate salt is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 18.1°2θ, 16.8°2θ, 9.0°2θ, and15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.8°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, and14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.8°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, and14.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.8°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, 14.2°2θ, 17.7°2θ,21.4°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate salt iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.8°2θ, 9.0°2θ, 15.7°2θ, 26.4°2θ, 14.2°2θ, 17.7°2θ,21.4°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate salt ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, or twelve XRPD signals selected from those set forth inTable 235.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,16.2°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at8.1°2θ, 16.2°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,16.2°2θ, 17.1°2θ, 23.7°2θ, and 25.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 8.1°2θ, 16.2°2θ, 17.1°2θ, 23.7°2θ, and 25.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,16.2°2θ, 17.1°2θ, 23.7°2θ, 25.8°2θ, 27.7°2θ, and 30.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals 8.1°2θ, 16.2°2θ, 17.1°2θ, 23.7°2θ,25.8°2θ, 27.7°2θ, and 30.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, or seven XRPD signalsselected from those set forth in Table 236.

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.8°2θ, 11.4°2θ, and 27.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at22.8°2θ, 11.4° 2θ, and 27.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.8°2θ, 11.4°2θ, 27.7°2θ, 24.7°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate is crystalline tabernanthalog sorbatecharacterized by XRPD signals at 22.8°2θ, 11.4°2θ, 27.7°2θ, 24.7°2θ, and12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.8°2θ, 11.4°2θ, 27.7°2θ, 24.7°2θ, 12.9°2θ, and 23.4°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog sorbate is crystalline tabernanthalog sorbatecharacterized by XRPD signals at 22.8°2θ, 11.4°2θ, 27.7°2θ, 24.7°2θ,12.9°2θ, and 23.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate ischaracterized by one, two, three, four, five, or six XRPD signalsselected from those set forth in Table 237.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, and 26.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, and26.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, 26.3°2θ, 22.9°2θ, and8.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 23.7°2θ,18.1°2θ, 16.7°2θ, 15.6°2θ, 26.3°2θ, 22.9°2θ, and 8.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, 26.3°2θ, 22.9°2θ, 8.9°2θ, 21.3°2θ,14.1°2θ, and 17.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, 26.3°2θ, 22.9°2θ, 8.9°2θ, 21.3°2θ,14.1°2θ, and 17.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, or thirteen XRPD signals selected from those setforth in Table 238.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, and 22.9°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, and22.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, 22.9°2θ, 26.3°2θ, and8.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 23.7°2θ,18.1°2θ, 16.7°2θ, 15.6°2θ, 22.9°2θ, 26.3°2θ, and 8.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, 22.9°2θ, 26.3°2θ, 8.9°2θ, 14.1°2θ,17.7°2θ, and 19.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.7°2θ, 15.6°2θ, 22.9°2θ, 26.3°2θ, 8.9°2θ, 14.1°2θ,17.7°2θ, and 19.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signalsselected from those set forth in Table 239.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,17.1°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at8.1°2θ, 17.1°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,17.1°2θ, 16.2°2θ, 23.7°2θ, and 25.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 8.1°2θ, 17.1°2θ, 16.2°2θ, 23.7°2θ, and 25.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,17.1°2θ, 16.2°2θ, 23.7°2θ, 25.8°2θ, 27.7°2θ, and 30.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 8.1°2θ, 17.1°2θ, 16.2°2θ, 23.7°2θ,25.8°2θ, 27.7°2θ, and 30.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, or seven XRPD signalsselected from those set forth in Table 240.

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.8°2θ, 11.4°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at22.8°2θ, 11.4° 20, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.8°2θ, 11.4°2θ, 12.9°2θ, 27.7°2θ, and 24.8°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate is crystalline tabernanthalog sorbatecharacterized by XRPD signals at 22.8°2θ, 11.4°2θ, 12.9°2θ, 27.7°2θ, and24.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate ischaracterized by one, two, three, four, or five XRPD signals selectedfrom those set forth in Table 241.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.6°2θ, 18.0°2θ, and 15.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.6°2θ, 18.0°2θ, and 15.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.6°2θ, 18.0°2θ, 15.6°2θ, 16.7°2θ, and 26.3°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.6°2θ, 18.0 °2θ, 15.6°2θ, 16.7°2θ,and 26.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.6°2θ, 18.0°2θ, 15.6°2θ, 16.7°2θ, 26.3°2θ, 22.9°2θ, and8.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 23.6°2θ,18.0°2θ, 15.6°2θ, 16.7°2θ, 26.3°2θ, 22.9°2θ, and 8.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.6°2θ, 18.0°2θ, 15.6°2θ, 16.7°2θ, 26.3°2θ, 22.9°2θ, 8.9°2θ, 21.3°2θ,17.6°2θ, and 28.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.6°2θ, 18.0°2θ, 15.6°2θ, 16.7°2θ, 26.3°2θ, 22.9°2θ, 8.9°2θ, 21.3°2θ,17.6°2θ, and 28.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, or fourteen XRPD signals selected fromthose set forth in Table 242.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.7°2θ, and 26.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 18.1°2θ, 16.7°2θ, 15.7°2θ, and26.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.7°2θ, 26.4°2θ, 9.0°2θ, and23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 23.7°2θ,18.1°2θ, 16.7°2θ, 15.7°2θ, 26.4°2θ, 9.0°2θ, and 23.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 15.7°2θ, 26.4°2θ, 9.0°2θ, 23.0°2θ, 21.4°2θ,14.2°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.7°2θ, 15.7°2θ, 26.4°2θ, 9.0°2θ, 23.0 °2θ, 21.4°2θ,14.2°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signalsselected from those set forth in Table 243.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,17.1°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at8.1°2θ, 17.1°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,17.1°2θ, 23.7°2θ, 25.8°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 8.1°2θ, 17.1°2θ, 23.7°2θ, 25.8°2θ, and 16.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,17.1°2θ, 23.7°2θ, 25.8°2θ, 16.2°2θ, 27.7°2θ, and 30.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 8.1°2θ, 17.1°2θ, 23.7°2θ, 25.8°2θ,16.2°2θ, 27.7°2θ, and 30.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,17.1°2θ, 23.7°2θ, 25.8°2θ, 16.2°2θ, 27.7°2θ, 30.0°2θ and19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 8.1°2θ,17.1°2θ, 23.7°2θ, 25.8°2θ, 16.2°2θ, 27.7°2θ, 30.0°2θ and19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, or eight XRPDsignals selected from those set forth in Table 244.

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.8°2θ, 11.4°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at22.8°2θ, 11.4°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.8°2θ, 11.4°2θ, 12.9°2θ, 27.7°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate is crystalline tabernanthalog sorbatecharacterized by XRPD signals at 22.8°2θ, 11.4°2θ, 12.9°2θ, 27.7°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate ischaracterized by one, two, three, four, or five XRPD signals selectedfrom those set forth in Table 245.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 18.1°2θ, and 15.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 15.7°2θ, 16.8°2θ, and 26.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 18.1°2θ, 15.7°2θ, 16.8°2θ, and26.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 15.7°2θ, 16.8°2θ, 26.4°2θ, 9.0°2θ, and23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 23.7°2θ,18.1°2θ, 15.7°2θ, 16.8°2θ, 26.4°2θ, 9.0°2θ, and 23.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 15.7°2θ, 16.8°2θ, 26.4°2θ, 9.0°2θ, 23.0°2θ, 14.2°2θ,17.7°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 15.7°2θ, 16.8°2θ, 26.4°2θ, 9.0°2θ, 23.0 °2θ, 14.2°2θ,17.7°2θ, and 21.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signalsselected from those set forth in Table 246.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 18.1°2θ, and 16.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ;Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 26.3°2θ, and 15.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 18.1°2θ, 16.7°2θ, 26.3°2θ, and15.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 26.3°2θ, 15.6°2θ, 22.9°2θ, and21.3°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 23.7°2θ,18.1°2θ, 16.7°2θ, 26.3°2θ, 15.6°2θ, 22.9°2θ, and 21.3°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 18.1°2θ, 16.7°2θ, 26.3°2θ, 15.6°2θ, 22.9°2θ, 21.3°2θ, 14.1°2θ,8.9°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at23.7°2θ, 18.1°2θ, 16.7°2θ, 26.3°2θ, 15.6°2θ, 22.9°2θ, 21.3°2θ, 14.1°2θ,8.9°2θ, and 17.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, or thirteen XRPD signals selected from those setforth in Table 247.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,23.7°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at8.1°2θ, 23.7°2θ, and 17.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,23.7°2θ, 17.1°2θ, 25.7°2θ, and 16.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 8.1°2θ, 23.7°2θ, 17.1°2θ, 25.7°2θ, and 16.2°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,23.7°2θ, 17.1°2θ, 25.7°2θ, 16.2°2θ, 27.6°2θ, and 30.0°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solidform of tabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 8.1°2θ, 23.7°2θ, 17.1°2θ, 25.7°2θ,16.2°2θ, 27.6°2θ, and 30.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 8.1°2θ,23.7°2θ, 17.1°2θ, 25.7°2θ, 16.2°2θ, 27.6°2θ, 30.0°2θ and19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 8.1°2θ,23.7°2θ, 17.1°2θ, 25.7°2θ, 16.2°2θ, 27.6°2θ, 30.0°2θ and19.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, or eight XRPDsignals selected from those set forth in Table 248.

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.7°2θ, 11.4°2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at22.7°2θ, 11.4° 2θ, and 12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of22.7°2θ, 11.4°2θ, 12.9°2θ, 27.7°2θ, and 24.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog sorbate is crystalline tabernanthalog sorbatecharacterized by XRPD signals at 22.7°2θ, 11.4°2θ, 12.9°2θ, 27.7°2θ, and24.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate ischaracterized by one, two, three, four, or five XRPD signals selectedfrom those set forth in Table 249.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.5°2θ, 16.5°2θ, and 20.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate characterized byXRPD signals at 19.5°2θ, 16.5°2θ, and 20.6°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratecharacterized by XRPD signals at 19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, and33.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by XRPD signals at19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, and33.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, 33.5°2θ and12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by XRPD signals at19.5°2θ, 16.5°2θ, 20.6°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, 33.5°2θ and12.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, eight, or nineXRPD signals selected from those set forth in Table 250.

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.6°2θ, 16.6°2θ, and 20.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0 °2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogmonofumarate is crystalline tabernanthalog monofumarate characterized byXRPD signals at 19.6°2θ, 16.6°2θ, and 20.7°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.6°2θ, 16.6°2θ, 20.7°2θ, 25.3°2θ, and 26.1°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog monofumarate is crystalline tabernanthalog monofumaratecharacterized by XRPD signals at 19.6°2θ, 16.6°2θ, 20.7°2θ, 25.3°2θ, and26.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.6°2θ, 16.6°2θ, 20.7°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, and33.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by XRPD signals at19.6°2θ, 16.6°2θ, 20.7°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, and33.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by two or more, orthree or more XRPD signals selected from the group consisting of19.6°2θ, 16.6°2θ, 20.7°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, 33.5°2θ, and13.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog monofumarate iscrystalline tabernanthalog monofumarate characterized by XRPD signals at19.6°2θ, 16.6°2θ, 20.7°2θ, 25.3°2θ, 26.1°2θ, 22.1°2θ, 33.5°2θ, and13.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog monofumarate ischaracterized by one, two, three, four, five, six, seven, or eight XRPDsignals selected from those set forth in Table 251.

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.3°2θ, 20.4°2θ, and 22.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, 22.4°2θ, 21.3°2θ, and 16.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog tartrate is crystalline tabernanthalog tartratecharacterized by XRPD signals at 17.3°2θ, 20.4°2θ, 22.4°2θ, 21.3°2θ, and16.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, 22.4°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, and19.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog tartrate is crystallinetabernanthalog tartrate characterized by XRPD signals at 17.3°2θ,20.4°2θ, 22.4°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, and 19.9°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.3°2θ, 20.4°2θ, 22.4°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, 19.9°2θ, 26.1°2θ,24.0°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.3°2θ, 20.4°2θ, 22.4°2θ, 21.3°2θ, 16.4°2θ, 28.3°2θ, 19.9°2θ, 26.1°2θ,24.0°2θ, and 16.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog tartrate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, eleven, twelve, thirteen, or fourteen XRPD signals selected fromthose set forth in Table 252.

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.4°2θ, 20.5°2θ, and 22.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.4°2θ, 20.5°2θ, and 22.5°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.4°2θ, 20.5°2θ, 22.5°2θ, 21.4°2θ, and 16.5°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog tartrate is crystalline tabernanthalog tartratecharacterized by XRPD signals at 17.4°2θ, 20.5°2θ, 22.5°2θ, 21.4°2θ, and16.5°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.4°2θ, 20.5°2θ, 22.5°2θ, 21.4°2θ, 16.5°2θ, 28.4°2θ, and 20.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In some embodiments,the solid form of tabernanthalog tartrate is crystalline tabernanthalogtartrate characterized by XRPD signals at 17.4°2θ, 20.5°2θ, 22.5°2θ,21.4°2θ, 16.5°2θ, 28.4°2θ, and 20.0°2θ (±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by two or more, orthree or more XRPD signals selected from the group consisting of17.4°2θ, 20.5°2θ, 22.5°2θ, 21.4°2θ, 16.5°2θ, 28.4°2θ, 20.0°2θ, 16.2°2θ,24.1°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog tartrate iscrystalline tabernanthalog tartrate characterized by XRPD signals at17.4°2θ, 20.5°2θ, 22.5°2θ, 21.4°2θ, 16.5°2θ, 28.4°2θ, 20.0°2θ, 16.2°2θ,24.1°2θ, and 26.2°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog tartrate ischaracterized by one, two, three, four, five, six, seven, eight, nine,ten, or eleven XRPD signals selected from those set forth in Table 253.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 9.0°2θ,18.0°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by XRPD signals at9.0°2θ, 18.0°2θ, and 23.7°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 9.0°2θ,18.0°2θ, 23.7°2θ, 9.1°2θ, and 27.1°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 9.0°2θ, 18.0°2θ, 23.7°2θ, 9.1°2θ, and 27.1°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, or five XRPD signals selectedfrom those set forth in Table 254.

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 9.0°2θ, and 26.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogbenzoate is crystalline tabernanthalog benzoate characterized by XRPDsignals at 23.7°2θ, 9.0°2θ, and 26.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 9.0°2θ, 26.4°2θ, 18.1°2θ, and 24.4°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation). In some embodiments, the solid form oftabernanthalog benzoate is crystalline tabernanthalog benzoatecharacterized by XRPD signals at 23.7°2θ, 9.0°2θ, 26.4°2θ, 18.1°2θ, and24.4°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the solid form of tabernanthalog benzoate iscrystalline tabernanthalog benzoate characterized by two or more, orthree or more XRPD signals selected from the group consisting of23.7°2θ, 9.0°2θ, 26.4°2θ, 18.1°2θ, 24.4°2θ, 19.7°2θ, and16.8°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). In someembodiments, the solid form of tabernanthalog benzoate is crystallinetabernanthalog benzoate characterized by XRPD signals at 23.7°2θ,9.0°2θ, 26.4°2θ, 18.1°2θ, 24.4°2θ, 19.7°2θ, and 16.8°2θ(±0.2°2θ;±0.1°2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog benzoate ischaracterized by one, two, three, four, five, six, seven, or eight XRPDsignals selected from those set forth in Table 255.

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.5°2θ, and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at5.7°2θ, 11.5°2θ, and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.5°2θ, 18.9°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation). In some embodiments, the solid form of tabernanthalogsorbate is crystalline tabernanthalog sorbate characterized by XRPDsignals at 5.7°2θ, 11.5°2θ, 18.9°2θ, and 23.0°2θ(±0.2°2θ; ±0.1°2θ; or±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate ischaracterized by one, two, three, or four XRPD signals selected fromthose set forth in Table 256.

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or 0.0°2θ; Cu Kα1 radiation). Insome embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by XRPD signals at5.7°2θ, 11.4°2θ, and 18.9°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; Cu Kα1radiation).

In some embodiments, the solid form of tabernanthalog sorbate iscrystalline tabernanthalog sorbate characterized by two or more, orthree or more XRPD signals selected from the group consisting of 5.7°2θ,11.4°2θ, 18.9°2θ, 18.8°2θ, and 24.6°2θ(±0.2°2θ; ±0.1°2θ; or ±0.0°2θ; CuKα1 radiation). In some embodiments, the solid form of tabernanthalogsorbate is crystalline tabernanthalog sorbate characterized by XRPDsignals at 5.7°2θ, 11.4°2θ, 18.9°2θ, 18.8°2θ, and 24.6°2θ(±0.2°2θ;±0.1°2θ; or ±0.0°2θ; Cu Kα1 radiation).

In some embodiments, the crystalline tabernanthalog sorbate ischaracterized by one, two, three, four, or five XRPD signals selectedfrom those set forth in Table 257.

Pharmaceutical Compositions and Formulations

In some embodiments, the present disclosure provides a pharmaceuticalcomposition comprising one or more of the salt or solid forms oftabernanthalog, illustrated above, and a pharmaceutically acceptableexcipient. Such compositions are suitable for administration to asubject, such as a human subject.

The presently disclosed pharmaceutical compositions can be prepared in awide variety of oral, parenteral, such as intravenous, and topicaldosage forms. Oral preparations include tablets, pills, powder,capsules, lozenges, cachets, slurries, suspensions, etc., suitable foringestion by the patient. The compositions of the present invention canalso be administered as solutions, orally or parenterally, such as byinjection, that is, intravenously, intramuscularly, intracutaneously,subcutaneously, intraduodenally, or intraperitoneally. Also, thecompositions described herein can be administered by inhalation, forexample, intranasally. Additionally, the compositions of the presentinvention can be administered transdermally. The compositions of thisinvention can also be administered by intraocular, intravaginal, andintrarectal routes including suppositories, insufflation, powders andaerosol formulations (for examples of steroid inhalants, see Rohatagi,J. Clin. Pharmacol. 35:1187-1193, 1995; Tjwa, Ann. Allergy AsthmaImmunol. 75:107-111, 1995). Accordingly, the present disclosure alsoprovides pharmaceutical compositions including a pharmaceuticallyacceptable carrier or excipient and the salt or solid form oftabernanthalog of the present disclosure.

For preparing pharmaceutical compositions from the compounds disclosedherein, pharmaceutically acceptable carriers can be either solid orliquid. Solid form preparations include powders, tablets, pills,capsules, cachets, suppositories, and dispersible granules. A solidcarrier can be one or more substances, which may also act as diluents,flavoring agents, binders, preservatives, tablet disintegrating agents,or an encapsulating material. Details on techniques for formulation andadministration are well described in the scientific and patentliterature, see, e.g., the latest edition of Remington's PharmaceuticalSciences, Mack Publishing Co, Easton Pa. (“Remington's”).

In powders, the carrier is a finely divided solid, which is in a mixturewith the finely divided active component. In tablets, the activecomponent is mixed with the carrier having the necessary bindingproperties in suitable proportions and compacted in the shape and sizedesired. The powders and tablets preferably contain from about 5% toabout 70% or from about 10% to about 70% of the compounds of the presentdisclosure.

Suitable solid excipients include, but are not limited to, magnesiumcarbonate; magnesium stearate; talc; pectin; dextrin; starch;tragacanth; a low melting wax; cocoa butter; carbohydrates; sugarsincluding, but not limited to, lactose, sucrose, mannitol, or sorbitol,starch from corn, wheat, rice, potato, or other plants; cellulose suchas methyl cellulose, hydroxypropylmethyl-cellulose, or sodiumcarboxymethylcellulose; and gums including arabic and tragacanth; aswell as proteins including, but not limited to, gelatin and collagen.

If desired, disintegrating or solubilizing agents may be added, such asthe cross-linked polyvinyl pyrrolidone, agar, alginic acid, or a saltthereof, such as sodium alginate.

For preparing suppositories, a low melting wax, such as a mixture offatty acid glycerides or cocoa butter, is first melted and the compoundsof the present invention are dispersed homogeneously therein, as bystirring. The molten homogeneous mixture is then poured into convenientsized molds, allowed to cool, and thereby to solidify.

Liquid form preparations include solutions and suspensions, for example,water or water/propylene glycol suspensions.

Aqueous suspensions suitable for oral use can be made by dispersing thefinely divided active component in water with viscous material, such asnatural or synthetic gums, resins, methylcellulose, sodiumcarboxymethylcellulose, hydroxypropylmethylcellulose, sodium alginate,polyvinylpyrrolidone, gum tragacanth and gum acacia, and dispersing orwetting agents such as a naturally occurring phosphatide (e.g.,lecithin), a condensation product of an alkylene oxide with a fatty acid(e.g., polyoxyethylene stearate), a condensation product of ethyleneoxide with a long chain aliphatic alcohol (e.g., heptadecaethyleneoxycetanol), a condensation product of ethylene oxide with a partialester derived from a fatty acid and a hexitol (e.g., polyoxyethylenesorbitol mono-oleate), or a condensation product of ethylene oxide witha partial ester derived from fatty acid and a hexitol anhydride (e.g.,polyoxyethylene sorbitan mono-oleate). The aqueous suspension can alsocontain one or more preservatives such as ethyl or n-propylp-hydroxybenzoate, one or more coloring agents, one or more flavoringagents and one or more sweetening agents, such as sucrose, aspartame orsaccharin. Formulations can be adjusted for osmolarity.

Also included are solid form preparations, which are intended to beconverted, shortly before use, to liquid form preparations for oraladministration. Such liquid forms include suspensions. Thesepreparations may contain, in addition to the active component,colorants, flavors, stabilizers, buffers, artificial and naturalsweeteners, dispersants, thickeners, solubilizing agents, and the like.

Oil suspensions can be formulated by suspending the compound of thepresent invention in a vegetable oil, such as arachis oil, olive oil,sesame oil or coconut oil, or in a mineral oil such as liquid paraffin;or a mixture of these. The oil suspensions can contain a thickeningagent, such as beeswax, hard paraffin or cetyl alcohol. Sweeteningagents can be added to provide a palatable oral preparation, such asglycerol, sorbitol or sucrose. These formulations can be preserved bythe addition of an antioxidant such as ascorbic acid. As an example ofan injectable oil vehicle, see Minto, J. Pharmacol. Exp. Ther.281:93-102, 1997. The pharmaceutical formulations of the invention canalso be in the form of oil-in-water emulsions. The oily phase can be avegetable oil or a mineral oil, described above, or a mixture of these.Suitable emulsifying agents include naturally occurring gums, such asgum acacia and gum tragacanth, naturally occurring phosphatides, such assoybean lecithin, esters or partial esters derived from fatty acids andhexitol anhydrides, such as sorbitan mono-oleate, and condensationproducts of these partial esters with ethylene oxide, such aspolyoxyethylene sorbitan mono-oleate. The emulsion can also containsweetening agents and flavoring agents, as in the formulation of syrupsand elixirs. Such formulations can also contain a demulcent, apreservative, or a coloring agent.

The compositions of the present disclosure can also be delivered asmicrospheres for slow release in the body. For example, microspheres canbe formulated for administration via intradermal injection ofdrug-containing microspheres, which slowly release subcutaneously (seeRao, J. Biomater Sci. Polym. Ed. 7:623-645, 1995; as biodegradable andinjectable gel formulations (see, e.g., Gao Pharm. Res. 12:857-863,1995); or, as microspheres for oral administration (see, e.g., Eyles, J.Pharm. Pharmacol. 49:669-674, 1997). Both transdermal and intradermalroutes afford constant delivery for weeks or months.

In some embodiments, the pharmaceutical compositions of the presentdisclosure can be formulated for parenteral administration, such asintravenous (IV) administration or administration into a body cavity orlumen of an organ. The formulations for administration will commonlycomprise a solution or suspension of the compositions of the presentdisclosure dissolved or suspended in a pharmaceutically acceptablecarrier. Among the acceptable vehicles and solvents that can be employedare water and Ringer's solution, an isotonic sodium chloride. Inaddition, sterile fixed oils can conventionally be employed as a solventor suspending medium. For this purpose, any bland fixed oil can beemployed including synthetic mono- or diglycerides. In addition, fattyacids such as oleic acid can likewise be used in the preparation ofinjectables. These solutions or suspensions are sterile and generallyfree of undesirable matter. These formulations may be sterilized byconventional, well known sterilization techniques. The formulations maycontain pharmaceutically acceptable auxiliary substances as required toapproximate physiological conditions such as pH adjusting and bufferingagents, toxicity adjusting agents, e.g., sodium acetate, sodiumchloride, potassium chloride, calcium chloride, sodium lactate and thelike. The concentration of the compositions of the present disclosure inthese formulations can vary widely, and will be selected primarily basedon fluid volumes, viscosities, body weight, and the like, in accordancewith the particular mode of administration selected and the patient'sneeds. For IV administration, the formulation can be a sterileinjectable preparation, such as a sterile injectable aqueous oroleaginous suspension. This suspension can be formulated according tothe known art using those suitable dispersing or wetting agents andsuspending agents. The sterile injectable preparation can also be asterile injectable solution or suspension in a nontoxicparenterally-acceptable diluent or solvent, such as a solution of1,3-butanediol.

In some embodiments, the formulations of the present disclosure can bedelivered using liposomes which fuse with the cellular membrane or areendocytosed, for example, by employing ligands attached to the liposome,or attached directly to the oligonucleotide, that bind to surfacemembrane protein receptors of the cell resulting in endocytosis. Byusing liposomes, particularly where the liposome surface carries ligandsspecific for target cells, or are otherwise preferentially directed to aspecific organ, one can focus the delivery of the compositions of thepresent invention into the target cells in vivo. (See, e.g.,Al-Muhammed, J. Microencapsul. 13:293-306, 1996; Chonn, Curr. Opin.Biotechnol. 6:698-708, 1995; Ostro, Am. J. Hosp. Pharm. 46:1576-1587,1989). In one embodiment, the compositions disclosed herein can alsocontain other compatible therapeutic agents. The compounds describedherein can be used in combination with at least one other active agent.

In another embodiment, the compositions disclosed herein can alsocontain other compatible therapeutic agents. The compounds describedherein can be used in combination with at least one other active agentknown to be useful in modulating a glucocorticoid receptor, or withadjunctive agents that may not be effective alone, but may contribute tothe efficacy of the active agent.

Administration:

The compositions of the present disclosure can be administered by anysuitable means, including oral, parenteral and topical methods.Transdermal administration methods, by a topical route, can beformulated as applicator sticks, suspensions, creams, ointments, pastes,jellies, paints, powders, and aerosols.

The pharmaceutical preparation is preferably in unit dosage form. Insuch form the preparation is subdivided into unit doses containingappropriate quantities of the compounds of the present invention. Theunit dosage form can be a packaged preparation, the package containingdiscrete quantities of preparation, such as packeted tablets, capsules,and powders in vials or ampoules. Also, the unit dosage form can be acapsule, tablet, cachet, or lozenge itself, or it can be the appropriatenumber of any of these in packaged form.

The salt and solid forms of tabernanthalog of the present invention canbe present in any suitable amount, and can depend on various factorsincluding, but not limited to, weight and age of the subject, state ofthe disease, and the like as is known to those of ordinary skill in theart.

The compound forms (salt and solid forms of tabernanthalog) disclosedherein also can be administered at any suitable frequency, interval andduration.

The compound forms of the present invention can be co-administered witha second active agent. In some embodiments, co-administration can beaccomplished by co-formulation, such as by preparing a singlepharmaceutical composition including both the compound form of thepresent disclosure (salt or solid form of tabernanthalog) and a secondactive agent. In other embodiments, the compound of the presentdisclosure and the second active agent can be formulated separately.

Methods of Treatment

In some embodiments, the salt and solid forms of the tabernanthalog ofthe present disclosure can be used to increase neuronal plasticity. Inother embodiments, the salt and solid forms of the tabernanthalog of thepresent disclosure can also be used to treat any brain disease. The saltand solid forms of the tabernanthalog of the present disclosure can alsobe used to increase at least one of translation, transcription orsecretion of neurotrophic factors.

In some embodiments, a compound of the present disclosure is used totreat neurological diseases. In some embodiments, the compound of thepresent disclosure has, for example, anti-addictive properties,antidepressant properties, anxiolytic properties, or a combinationthereof. In some embodiments, the neurological disease is aneuropsychiatric disease. In some embodiments, the neuropsychiatricdisease is a mood or anxiety disorder. In some embodiments, theneurological disease is a migraine, headaches (e.g., cluster headache),post-traumatic stress disorder (PTSD), anxiety, depression,neurodegenerative disorder, Alzheimer's disease, Parkinson's disease,psychological disorder, treatment resistant depression, suicidalideation, major depressive disorder, bipolar disorder, schizophrenia,stroke, traumatic brain injury, and addiction (e.g., substance usedisorder). In some embodiments, the neurological disease is a migraineor cluster headache. In some embodiments, the neurological disease is aneurodegenerative disorder, Alzheimer's disease, or Parkinson's disease.In some embodiments, the neurological disease is a psychologicaldisorder, treatment resistant depression, suicidal ideation, majordepressive disorder, bipolar disorder, schizophrenia, post-traumaticstress disorder (PTSD), addiction (e.g., substance use disorder),depression, or anxiety. In some embodiments, the neuropsychiatricdisease is a psychological disorder, treatment resistant depression,suicidal ideation, major depressive disorder, bipolar disorder,schizophrenia, post-traumatic stress disorder (PTSD), addiction (e.g.,substance use disorder), depression, or anxiety. In some embodiments,the neuropsychiatric disease or neurological disease is post-traumaticstress disorder (PTSD), addiction (e.g., substance use disorder),schizophrenia, depression, or anxiety. In some embodiments, theneuropsychiatric disease or neurological disease is addiction (e.g.,substance use disorder). In some embodiments, the neuropsychiatricdisease or neurological disease is depression. In some embodiments, theneuropsychiatric disease or neurological disease is anxiety. In someembodiments, the neuropsychiatric disease or neurological disease ispost-traumatic stress disorder (PTSD). In some embodiments, theneurological disease is stroke or traumatic brain injury. In someembodiments, the neuropsychiatric disease or neurological disease isschizophrenia.

In some embodiments, a compound of the present disclosure is used toincrease neuronal plasticity. In some embodiments, the compounds of thepresent disclosure are used to treat a brain disorder. In someembodiments, the compounds of the present disclosure are used toincrease at least one of translation, transcription, or secretion ofneurotrophic factors.

In some embodiments, the present disclosure provides a method oftreating a disease, including administering to a subject in needthereof, a therapeutically effective amount of a compound of the presentdisclosure. In some embodiments, the disease is a musculoskeletal paindisorder including fibromyalgia, muscle pain, joint stiffness,osteoarthritis, rheumatoid arthritis, muscle cramps. In someembodiments, the present invention provides a method of treating adisease of women's reproductive health including premenstrual dysphoricdisorder (PMDD), premenstrual syndrome (PMS), post-partum depression,and menopause.

In some embodiments, the salt and solid forms of tabernanthalog of thepresent disclosure have activity as 5-HT_(2A) modulators. In someembodiments, the compounds of the present disclosure elicit a biologicalresponse by activating the 5-HT_(2A) receptor (e.g., allostericmodulation or modulation of a biological target that activates the5-HT_(2A) receptor). 5-HT_(2A) agonism has been correlated with thepromotion of neural plasticity (Ly et al., Cell Rep. 2018 Jun. 12;23(11):3170-3182). 5-HT_(2A) antagonists abrogate the neuritogenesis andspinogenesis effects of hallucinogenic compounds with 5-HT_(2A) agonistactivity, for example, DMT, LSD, and DOI. In some embodiments, thecompounds of the present disclosure are 5-HT_(2A) modulators and promoteneural plasticity (e.g., cortical structural plasticity). In someembodiments, the compounds of the present disclosure are selective5-HT_(2A) modulators and promote neural plasticity (e.g., corticalstructural plasticity). In some embodiments, promotion of neuralplasticity includes, for example, increased dendritic spine growth,increased synthesis of synaptic proteins, strengthened synapticresponses, increased dendritic arbor complexity, increased dendriticbranch content, increased spinogenesis, increased neuritogenesis, or anycombination thereof. In some embodiments, increased neural plasticityincludes, for example, increased cortical structural plasticity in theanterior parts of the brain.

In some embodiments, the 5-HT_(2A) modulators (e.g., 5-HT_(2A) agonists)are non-hallucinogenic. In some embodiments, non-hallucinogenic5-HT_(2A) modulators (e.g., 5-HT_(2A) agonists) are used to treatneurological diseases, which modulators do not elicit dissociativeside-effects. In some embodiments, the hallucinogenic potential of thecompounds of the present disclosure described herein is assessed invitro. In some embodiments, the hallucinogenic potential assessed invitro of the compounds of the present disclosure is compared to thehallucinogenic potential assessed in vitro of hallucinogenic homologs.In some embodiments, the compounds of the present disclosure elicit lesshallucinogenic potential in vitro than the hallucinogenic homologs.

In some embodiments, serotonin receptor modulators, such as modulatorsof serotonin receptor 2A (5-HT_(2A) modulators, e.g., 5-HT_(2A)agonists), are used to treat a brain disorder. The presently disclosedcompounds (salt and solid forms of tabernanthalog) can function as5-HT_(2A) agonists alone, or in combination with a second therapeuticagent that also is a 5-HT_(2A) modulator. In such cases the secondtherapeutic agent can be an agonist or an antagonist. In some instances,it may be helpful administer a 5-HT_(2A) antagonist in combination witha compound of the present disclosure to mitigate undesirable effects of5-HT_(2A) agonism, such as potential hallucinogenic effects. Serotoninreceptor modulators useful as second therapeutic agents for combinationtherapy as described herein are known to those of skill in the art andinclude, without limitation, ketanserin, volinanserin (MDL-100907),eplivanserin (SR-46349), pimavanserin (ACP-103), glemanserin(MDL-11939), ritanserin, flibanserin, nelotanserin, blonanserin,mianserin, mirtazapine, roluperiodone (CYR-101, MIN-101), quetiapine,olanzapine, altanserin, acepromazine, nefazodone, risperidone,pruvanserin, AC-90179, AC-279, adatanserin, fananserin, HY10275,benanserin, butanserin, manserin, iferanserin, lidanserin, pelanserin,seganserin, tropanserin, lorcaserin, ICI-169369, methiothepin,methysergide, trazodone, cinitapride, cyproheptadine, brexpiprazole,cariprazine, agomelatine, setoperone, 1-(1-Naphthyl)piperazine,LY-367265, pirenperone, metergoline, deramciclane, amperozide,cinanserin, LY-86057, GSK-215083, cyamemazine, mesulergine, BF-1,LY-215840, sergolexole, spiramide, LY-53857, amesergide, LY-108742,pipamperone, LY-314228, 5-I-R91150, 5-MeO-NBpBrT,9-Aminomethyl-9,10-dihydroanthracene, niaprazine, SB-215505, SB-204741,SB-206553, SB-242084, LY-272015, SB-243213, SB-200646, RS-102221,zotepine, clozapine, chlorpromazine, sertindole, iloperidone,paliperidone, asenapine, amisulpride, aripiprazole, lurasidone,ziprasidone, lumateperone, perospirone, mosapramine, AMDA(9-Aminomethyl-9,10-dihydroanthracene), methiothepin, anextended-release form of olanzapine (e.g., ZYPREXA RELPREVV), anextended-release form of quetiapine, an extended-release form ofrisperidone (e.g., Risperdal Consta), an extended-release form ofpaliperidone (e.g., Invega Sustenna and Invega Trinza), anextended-release form of fluphenazine decanoate including ProlixinDecanoate, an extended-release form of aripiprazole lauroxil includingAristada, and an extended-release form of aripiprazole including AbilifyMaintena, or a pharmaceutically acceptable salt, solvate, metabolite,derivative, or prodrug thereof. In some embodiments, the serotoninreceptor modulator used as a second therapeutic is pimavanserin or apharmaceutically acceptable salt, solvate, metabolite, derivative, orprodrug thereof.

In some embodiments, the serotonin receptor modulator is administeredprior to a compound of the present disclosure, such as about three orabout one hours prior to the administration of a compound of the presentdisclosure. In some embodiments, the serotonin receptor modulator isadministered at most about one hour prior to the presently disclosedcompound. Thus, in some embodiments of combination therapy with thepresently disclosed compounds, the second therapeutic agent is aserotonin receptor modulator.

In some embodiments, the salt and solid forms of the tabernanthalog actas non-hallucinogenic 5-HT2_(A) modulators (e.g., 5-HT2_(A) agonists)that are used to treat neurological diseases. In some embodiments, theneurological diseases comprise decreased neural plasticity, decreasedcortical structural plasticity, decreased 5-HT_(2A) receptor content,decreased dendritic arbor complexity, loss of dendritic spines,decreased dendritic branch content, decreased spinogenesis, decreasedneuritogenesis, retraction of neurites, or any combination thereof.

In some embodiments, the salt and solid forms of the tabernanthalog actas non-hallucinogenic 5-HT_(2A) modulators (e.g., 5-HT_(2A) agonists)are used for increasing neuronal plasticity. In some embodiments,non-hallucinogenic 5-HT_(2A) modulators (e.g., 5-HT_(2A) agonists) areused for treating a brain disorder. In some embodiments,non-hallucinogenic 5-HT_(2A) modulators (e.g., 5-FIT_(2A) agonists) areused for increasing at least one of translation, transcription, orsecretion of neurotrophic factors.

Methods for Increasing Neuronal Plasticity

Neuronal plasticity refers to the ability of the brain to changestructure and/or function throughout a subject's life. New neurons canbe produced and integrated into the central nervous system throughoutthe subject's life. Increasing neuronal plasticity includes, but is notlimited to, promoting neuronal growth, promoting neuritogenesis,promoting synaptogenesis, promoting dendritogenesis, increasingdendritic arbor complexity, increasing dendritic spine density, andincreasing excitatory synapsis in the brain. In some embodiments,increasing neuronal plasticity comprises promoting neuronal growth,promoting neuritogenesis, promoting synaptogenesis, promotingdendritogenesis, increasing dendritic arbor complexity, and increasingdendritic spine density.

In some embodiments, increasing neuronal plasticity by treating asubject with a salt or solid form of tabernanthalog can treatneurodegenerative disorder, Alzheimer's, Parkinson's disease,psychological disorder, depression, addiction, anxiety, post-traumaticstress disorder, treatment resistant depression, suicidal ideation,major depressive disorder, bipolar disorder, schizophrenia, stroke,traumatic brain injury, or substance use disorder.

In some embodiments, the present disclosure provides methods forincreasing neuronal plasticity, comprising contacting a neuronal cellwith a compound of the present disclosure. In some embodiments,increasing neuronal plasticity improves a brain disorder describedherein.

In some embodiments, a compound of the present disclosure is used toincrease neuronal plasticity. In some embodiments, the compounds used toincrease neuronal plasticity have, for example, anti-addictiveproperties, antidepressant properties, anxiolytic properties, or acombination thereof. In some embodiments, decreased neuronal plasticityis associated with a neuropsychiatric disease. In some embodiments, theneuropsychiatric disease is a mood or anxiety disorder. In someembodiments, the neuropsychiatric disease includes, for example,migraine, cluster headache, post-traumatic stress disorder (PTSD),schizophrenia, anxiety, depression, and addiction (e.g., substance abusedisorder). In some embodiments, brain disorders include, for example,migraines, addiction (e.g., substance use disorder), depression, andanxiety.

In some embodiments, the experiment or assay to determine increasedneuronal plasticity of any compound of the present disclosure is aphenotypic assay, a dendritogenesis assay, a spinogenesis assay, asynaptogenesis assay, a Sholl analysis, a concentration-responseexperiment, a 5-HT_(2A) agonist assay, a 5-HT_(2A) antagonist assay, a5-HT_(2A) binding assay, or a 5-HT_(2A) blocking experiment (e.g.,ketanserin blocking experiments). In some embodiments, the experiment orassay to determine the hallucinogenic potential of any compound of thepresent invention is a mouse head-twitch response (HTR) assay.

In some embodiments, the present disclosure provides a method forincreasing neuronal plasticity, comprising contacting a neuronal cellwith a compound disclosed herein.

Methods of Treating a Brain Disorder

In some embodiments, the present disclosure provides a method oftreating a disease, including administering to a subject in needthereof, a therapeutically effective amount of a salt or solid form oftabernanthalog of the present disclosure. In some embodiments, thedisease is a musculoskeletal pain disorder including fibromyalgia,muscle pain, joint stiffness, osteoarthritis, rheumatoid arthritis,muscle cramps. In some embodiments, the present disclosure provides amethod of treating a disease of women's reproductive health includingpremenstrual dysphoric disorder (PMDD), premenstrual syndrome (PMS),post-partum depression, and menopause. In some embodiments, the presentdisclosure provides a method of treating a brain disorder, includingadministering to a subject in need thereof, a therapeutically effectiveamount of a compound of the present disclosure. In some embodiments, thepresent disclosure provides a method of treating a brain disorder withcombination therapy, including administering to a subject in needthereof, a therapeutically effective amount of a compound of the presentdisclosure and at least one additional therapeutic agent.

In some embodiments, 5-HT_(2A) modulators (e.g., 5-HT_(2A) agonists) areused to treat a brain disorder. In some embodiments, the brain disorderscomprise decreased neural plasticity, decreased cortical structuralplasticity, decreased 5-HT_(2A) receptor content, decreased dendriticarbor complexity, loss of dendritic spines, decreased dendritic branchcontent, decreased spinogenesis, decreased neuritogenesis, retraction ofneurites, or any combination thereof.

In some embodiments, a compound of the present disclosure is used totreat brain disorders. In some embodiments, the compounds have, forexample, anti-addictive properties, antidepressant properties,anxiolytic properties, or a combination thereof. In some embodiments,the brain disorder is a neuropsychiatric disease. In some embodiments,the neuropsychiatric disease is a mood or anxiety disorder. In someembodiments, brain disorders include, for example, migraine, clusterheadache, post-traumatic stress disorder (PTSD), anxiety, depression,panic disorder, suicidality, schizophrenia, and addiction (e.g.,substance abuse disorder). In some embodiments, brain disorders include,for example, migraines, addiction (e.g., substance use disorder),depression, and anxiety.

In some embodiments, the present disclosure provides a method oftreating a brain disorder, comprising administering to a subject in needthereof a therapeutically effective amount of a compound disclosedherein.

In some embodiments, the brain disorder is a neurodegenerative disorder,Alzheimer's, Parkinson's disease, psychological disorder, depression,addiction, anxiety, post-traumatic stress disorder, treatment resistantdepression, suicidal ideation, major depressive disorder, bipolardisorder, schizophrenia, stroke, traumatic brain injury, or substanceuse disorder.

In some embodiments, the brain disorder is a neurodegenerative disorder,Alzheimer's, or Parkinson's disease. In some embodiments, the braindisorder is a psychological disorder, depression, addiction, anxiety, ora post-traumatic stress disorder. In some embodiments, the braindisorder is depression. In some embodiments, the brain disorder isaddiction. In some embodiments, the brain disorder is treatmentresistant depression, suicidal ideation, major depressive disorder,bipolar disorder, schizophrenia, stroke, traumatic brain injury orsubstance use disorder. In some embodiments, the brain disorder istreatment resistant depression, suicidal ideation, major depressivedisorder, bipolar disorder, schizophrenia, or substance use disorder. Insome embodiments, the brain disorder is stroke or traumatic braininjury. In some embodiments, the brain disorder is treatment resistantdepression, suicidal ideation, major depressive disorder, bipolardisorder, or substance use disorder. In some embodiments, the braindisorder is schizophrenia. In some embodiments, the brain disorder isalcohol use disorder.

In some embodiments, the method further comprises administering one ormore additional therapeutic agent that is lithium, olanzapine (Zyprexa),quetiapine (Seroquel), risperidone (Risperdal), aripiprazole (Abilify),ziprasidone (Geodon), clozapine (Clozaril), divalproex sodium(Depakote), lamotrigine (Lamictal), valproic acid (Depakene),carbamazepine (Equetro), topiramate (Topamax), levomilnacipran(Fetzima), duloxetine (Cymbalta, Yentreve), venlafaxine (Effexor),citalopram (Celexa), fluvoxamine (Luvox), escitalopram (Lexapro),fluoxetine (Prozac), paroxetine (Paxil), sertraline (Zoloft),clomipramine (Anafranil), amitriptyline (Elavil), desipramine(Norpramin), imipramine (Tofranil), nortriptyline (Pamelor), phenelzine(Nardil), tranylcypromine (Parnate), diazepam (Valium), alprazolam(Xanax), or clonazepam (Klonopin).

In certain embodiments of the method for treating a brain disorder witha solid form disclosed herein, a second therapeutic agent that is anempathogenic agent is administered. Examples of suitable empathogenicagents for use in combination with the present solid forms includephenethylamines, such as 3,4-methylene-dioxymethamphetamine (MDMA), andanalogs thereof.

Other suitable empathogenic agents for use in combination with thepresently disclosed salts and solid forms include, without limitation,

-   N-Allyl-3,4-methylenedioxy-amphetamine (MDAL)-   N-Butyl-3,4-methylenedioxyamphetamine (MDBU)-   N-Benzyl-3,4-methylenedioxyamphetamine (MDBZ)-   N-Cyclopropylmethyl-3,4-methylenedioxyamphetamine (MDCPM)-   N,N-Dimethyl-3,4-methylenedioxyamphetamine (MDDM)-   N-Ethyl-3,4-methylenedioxyamphetamine (MDE; MDEA)-   N-(2-Hydroxyethyl)-3,4-methylenedioxy amphetamine (MDHOET)-   N-Isopropyl-3,4-methylenedioxyamphetamine (MDIP)-   N-Methyl-3,4-ethylenedioxyamphetamine (MDMC)-   N-Methoxy-3,4-methylenedioxyamphetamine (MDMEO)-   N-(2-Methoxyethyl)-3,4-methylenedioxyamphetamine (MDMEOET)-   alpha,alpha,N-Trimethyl-3,4-methylenedioxyphenethylamine (MDMP;    3,4-Methylenedioxy-N-methylphentermine)-   N-Hydroxy-3,4-methylenedioxyamphetamine (MDOH)-   3,4-Methylenedioxyphenethylamine (MDPEA)-   alpha,alpha-Dimethyl-3,4-methylenedioxyphenethylamine (MDPH;    3,4-methylenedioxyphentermine)-   N-Propargyl-3,4-methylenedioxyamphetamine (MDPL)-   Methylenedioxy-2-aminoindane (MDAI)-   1,3-Benzodioxolyl-N-methylbutanamine MBDB-   3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine-   3,4-Methylenedioxyamphetamine MDA-   Methylone (also known as “3,4-methylenedioxy-N-methylcathinone-   Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone GHB or    Gamma Hydroxybutyrate or sodium oxybate-   N-Propyl-3,4-methylenedioxyamphetamine (MDPR), and the like.

In some embodiments, the compounds of the present disclosure are used incombination with the standard of care therapy for a neurological diseasedescribed herein. Non-limiting examples of the standard of caretherapies, may include, for example, lithium, olanzapine, quetiapine,risperidone, aripiprazole, ziprasidone, clozapine, divalproex sodium,lamotrigine, valproic acid, carbamazepine, topiramate, levomilnacipran,duloxetine, venlafaxine, citalopram, fluvoxamine, escitalopram,fluoxetine, paroxetine, sertraline, clomipramine, amitriptyline,desipramine, imipramine, nortriptyline, phenelzine, tranylcypromine,diazepam, alprazolam, clonazepam, or any combination thereof.Nonlimiting examples of standard of care therapy for depression aresertraline, fluoxetine, escitalopram, venlafaxine, or aripiprazole.Non-limiting examples of standard of care therapy for depression arecitralopram, escitalopram, fluoxetine, paroxetine, diazepam, orsertraline. Additional examples of standard of care therapeutics areknown to those of ordinary skill in the art.

Methods of Increasing at Least One of Translation, Transcription, orSecretion of Neurotrophic Factors

Neurotrophic factors refer to a family of soluble peptides or proteinswhich support the survival, growth, and differentiation of developingand mature neurons. Increasing at least one of translation,transcription, or secretion of neurotrophic factors can be useful for,but not limited to, increasing neuronal plasticity, promoting neuronalgrowth, promoting neuritogenesis, promoting synaptogenesis, promotingdendritogenesis, increasing dendritic arbor complexity, increasingdendritic spine density, and increasing excitatory synapsis in thebrain. In some embodiments, increasing at least one of translation,transcription, or secretion of neurotrophic factors can increasingneuronal plasticity. In some embodiments, increasing at least one oftranslation, transcription, or secretion of neurotrophic factors canpromoting neuronal growth, promoting neuritogenesis, promotingsynaptogenesis, promoting dendritogenesis, increasing dendritic arborcomplexity, and/or increasing dendritic spine density.

In some embodiments, 5-HT_(2A) modulators (e.g., 5-HT_(2A) agonists) areused to increase at least one of translation, transcription, orsecretion of neurotrophic factors. In some embodiments, a compound ofthe present disclosure is used to increase at least one of translation,transcription, or secretion of neurotrophic factors. In someembodiments, increasing at least one of translation, transcription orsecretion of neurotrophic factors treats a migraine, headaches (e.g.,cluster headache), post-traumatic stress disorder (PTSD), anxiety,depression, neurodegenerative disorder, Alzheimer's disease, Parkinson'sdisease, psychological disorder, treatment resistant depression,suicidal ideation, major depressive disorder, bipolar disorder,schizophrenia, stroke, traumatic brain injury, and addiction (e.g.,substance use disorder).

In some embodiments, the experiment or assay used to determine increasetranslation of neurotrophic factors includes ELISA, western blot,immunofluorescence assays, proteomic experiments, and mass spectrometry.In some embodiments, the experiment or assay used to determine increasetranscription of neurotrophic factors includes gene expression assays,PCR, and microarrays. In some embodiments, the experiment or assay usedto determine increase secretion of neurotrophic factors includes ELISA,western blot, immunofluorescence assays, proteomic experiments, and massspectrometry.

In some embodiments, the present disclosure provides a method forincreasing at least one of translation, transcription or secretion ofneurotrophic factors, comprising contacting a neuronal cell with acompound disclosed herein.

EXAMPLES

In the following Examples, the relative intensity values in peak tableswere calculated using the Net. intensity values.

Example 1: Polymorph Production of Tabernanthalog Fumarate

The active pharmaceutical ingredient (API), tabernanthalog fumarate, ischaracterized to evaluate its physical properties. The evaluation isperformed by X-ray powder diffraction (XRPD), polarized light microscopy(PLM), differential scanning calorimetry (DSC), thermogravimetry (TG),dynamic vapor sorption/desorption (DVS), and/or solubility testing inorganic solvents, water, and mixed solvent systems. XRPD data is used toassess crystallinity. PLM data is used to evaluate crystallinity andparticle size/morphology. DSC data is used to evaluate melting point,thermal stability, and crystalline form conversion. TG data is used toevaluate if the API is a solvate or hydrate, and to evaluate thermalstability. DVS data is used to evaluate hygroscopicity of the API and ifhydrates can be formed at high relative humidity. About 10 to 15solvents may be selected from Table 2, based on their properties(polarity, dielectric constant, and dipole moment).

TABLE 2 List of Solvents Solvents acetic acid n-heptane acetone n-hexaneacetonitrile 1,1,1,3,3,3-hexafluoro-2-propanol benzyl alcohol isobutanol(2-methyl-1-propanol) 1-butanol isopentanol (3-methyl-1-butanol)2-butanol isopropyl alcohol (2-propanol) butyl acetate isopropylbenzene(cumene) t-butyl methyl ether methanol chlorobenzene methoxybenzene(anisole) chloroform methyl acetate di(ethylene glycol) methyl ethylketone (2-butanone) dichloromethane methyl isobutyl ketone diethyl ethernitromethane diethylamine N-methyl-2-pyrrolidone (NMP) Dimethylacetamide(DMA) 1-octanol diisopropyl ether 1-pentanol N,N-dimethyl-formamide(DMF) 1-propanol dimethyl sulfoxide perfluorohexane 1,4-dioxane propylacetate 1,2-ethanediol (ethylene glycol) 1,1,2,2-tetrachloroethaneethanol tetrahydrofuran ethanolamine toluene 2-ethoxyethanol(Cellosolve) 1,1,1-trichloroethane ethyl acetate 2,2,2-trifluoroethanolethyl formate water formic acid o-xylene (1,2-dimethylbenzene) glycerolp-xylene (1,4-dimethylbenzene)

The information obtained is used for designing the subsequent polymorphscreen. Solvents are used as a single solvent or as solvent mixtures,some containing water. The techniques used for the polymorph screen arechosen based on the solvent selected and properties of the API. Thefollowing techniques (or a combination of techniques) may be used forthe polymorph screening:

-   -   API is dissolved in a solvent or mixture of solvents, and the        solvents are evaporated at different rates (slow evaporation or        fast evaporation) and at different temperatures (ambient or        elevated).    -   API is dissolved in a solvent or mixture of solvents (at ambient        temperature or an elevated temperature), and the final solution        is cooled (between −78° C. to 20° C.). The cooling method can be        a fast cooling (by plunging the sample to an ice bath or a dry        ice/acetone bath), or slow cooling. The solids formed will be        recovered by filtration and dried (air dried or vacuum dried).    -   API is dissolved in a solvent or mixture of solvents, and an        antisolvent is added to precipitate the salt. The solids formed        will be recovered by filtration and dried (air dried or vacuum        dried).    -   API is added to a solvent or mixture of solvents, where the API        is not fully dissolved. The slurry will be agitated at different        temperatures for a number of days. The solids formed will be        recovered by filtration and (air dried or vacuum dried).    -   API is milled (by mechanical milling or by mortar and pestle),        with a drop of solvent, or without any solvent.    -   API is melted and cooled (at different cooling rates, fast and        slow, and cooled to different temperatures) to obtain solids.    -   API is suspended in a solvent or mixture of solvents, and the        slurry is placed in a heating/cooling cycle for multiple cycles.        The remaining solids after the final cooling cycle will be        filtered and (air dried or vacuum dried).    -   API is processed to obtain an amorphous form (by melting,        milling, solvent evaporation, spray drying or lyophilization).        The amorphous form will then be exposed to elevated humidity (or        elevated temperature, or combination thereof), or to solvent        vapors for extended period of days.    -   API is exposed to elevated humidity (or elevated temperature, or        combination thereof), or to solvent vapors for extended period        of days.    -   Two or more polymorphs of the API are mixed in a solvent or        solvent systems (some solvent mixtures containing variable        amount of water) to obtain a slurry, and the slurry will be        agitated (at various temperatures) for an extended period of        time (days). The solvent system used can be pre-saturated with        the API. The final solids will be filtered and dried (air dried        or vacuum dried).    -   API is heated to a specific temperature and cooled (at ambient        conditions or in a dry box).

The solids obtained are analyzed by XRPD to determine if they arecrystalline and, if so, by DSC to see the melting point and by TG to seeif they are hydrated/solvated, and by ¹H NMR spectroscopy to ensurechemical integrity. Karl Fischer water titration is performed on formsthat are hydrated. DVS analysis is performed to evaluate hygroscopicityof the form and if hydrated form is present. In particular, variabletemperature analyses, including variable temperature XRPD, are performedto assess the stability of each physical form as well as itscrystallinity.

Differential scanning calorimetry (DSC) thermograms are obtained using aDSC Q 100 (TA Instruments, New Castle, Del.). The temperature axis andcell constant of the DSC cell are calibrated with indium (10 mg, 99.9%pure, melting point 156.6° C., heat of fusion 28.4 J/g). Samples(2.0-5.0 mg) are weighed in aluminum pans on an analytical balance.Aluminum pans without lids are used for the analysis. The samples areequilibrated at 25° C. and heated to 250-300° C. at a heating rate of10° C./min under continuous nitrogen flow. TG analysis of the samples isperformed with a Q 50(TA Instruments, New Castle, Del.). Samples(2.0-5.0 mg) are analyzed in open aluminum pans under a nitrogen flow(50 mL/min) at 25° C. to 210° C. with a heating rate of 10° C./min.

The sample for moisture analysis is allowed to dry at 25° C. for up to 4hours under a stream of dry nitrogen. The relative humidity is thenincreased stepwise from 10 to 90% relative humidity (adsorption scan)allowing the sample to equilibrate for a maximum of four hours beforeweighing and moving onto the next step. The desorption scan is measuredfrom 85 to 0% relative humidity with the same equilibration time. Thesample is then dried under a stream of dry nitrogen at 80° C. for 2hours or until no weight loss is observed.

X-ray powder diffraction data are collected using a Miniflex TabletopXRD system (Rigaku/MSC, The Woodlands, Tex.) from 5° to 45° 2θ withsteps of 0.1°, and the measuring time is 1.0 second/step. All samplesare ground to similar size before exposure to radiation. The powdersamples are illuminated using CuKα radiation (λ=1.54056 Å) at 30 kV and15 mA.

Variable temperature XRPD data are collected using a Huber Imaging PlateGuinier Camera 670 employing Ni-filtered CuKα₁ radiation (λ=1.5405981 Å)produced at 40 kV and 20 mA by a Philips PW1120/00 generator fitted witha Huber long fine-focus tube PW2273/20 and a Huber Guinier MonochromatorSeries 611/15. The original powder is packed into a Lindemann capillary(Hilgenberg, Germany) with an internal diameter of 1 mm and a wallthickness of 0.01 mm. The sample is heated at an average rate of 5Kmin⁻¹ using a Huber High Temperature Controller HTC 9634 unit with thecapillary rotation device 670.2. The temperature is held constant atselected intervals for 10 min while the sample is exposed to X-rays andmultiple scans are recorded. A 2θ-range of 4.00-100.0° is used with astep size of 0.005° 2θ.

In certain embodiments wherein the solid form is a solvate, such as ahydrate, the DSC thermogram reveals endothermic transitions. Inaccordance with the observed DSC transitions, TGA analysis indicatesstages of weight change corresponding to desolvation or dehydrationand/or melting of the sample. In the case of hydrates, these results arein harmony with Karl Fisher titration data which indicate the watercontent of the sample.

The moisture sorption profile of a sample can be generated to assess thestability of a solid form is stable over a range of relative humidities.In certain embodiments, the change in moisture content over 10.0 to95.0% relative humidity is small. In other embodiments the change inmoisture content over 10.0 to 95.0% relative humidity is reversible.

In certain embodiments, the XRPD pattern of a sample of solid formindicates that the sample has a well-defined crystal structure and ahigh degree of crystallinity.

Example 2: Preparation of Tabernanthalog Fumarate

Tabernanthalog fumarate was prepared according to WO 2020/176599.Analysis of the fumarate salt using thermal techniques suggest apropensity to form solvates and to disproportionate into thehemi-fumarate salt and/or the free base and non-associated fumaric acid.Accordingly improved forms of the molecule were sought.

Solubility assessment of tabernanthalog fumarate revealed only sparingsolubility in a variety of solvents. Consistent with Example 1, sampleswere dissolved in various solvents/solvent systems and cooled to isolatesolid material.

Tabernanthalog fumarate dissolved at 5 vol (200 mg/mL) only at reflux intwo solvents, water and methanol. At 15 vol the product dissolved inboth refluxing butanol and ethanol. Consistent with Example 1, thedissolved samples were cooled. On cooling, each of the four effectivesolvents yielded solid material. The solids thus obtained were analyzedby XRPD yielding diffractograms with novel peaks from products isolatedfrom each of the four protic solvents.

The sample isolated from butanol comprised crystalline materialresponsible for the XRPD diffractogram of FIG. 1 . Such material isreferred to as Pattern #15 herein.

A sample isolated from ethanol (reflux 20 vol followed by cooling)yielded solid crystalline material having Pattern #5, as illustrated byFIG. 2 .

A sample was isolated from IPA (isopropanol)/heptanes (10 vol IPA/5 volheptanes stirred at 40° C.), yielding material comprising crystallinetabernanthalog hemifumarate salt having XRPD Pattern #21, as illustratedin FIG. 5 .

A sample was crystallized from purified water, yielding crystallinetabernanthalog fumarate characterized by the XRPD diffractogram providedas FIG. 14 , with the top trace produced from an oven-dried crystallinesample, the middle trace produced from the sample prior to drying. Thebottom trace of FIG. 14 was obtained from an alternate crystalline formof tabernanthalog fumarate.

A sample was crystallized from methanol yielding tabernanthalog fumaratecharacterized by the XRPD diffractogram provided as FIG. 15 , with thetop trace produced from an oven-dried crystalline sample, the middletrace produced from the sample prior to drying. The bottom trace of FIG.15 was obtained from an alternate crystalline form of tabernanthalogfumarate.

Example 3: Polymorph Production of Tabernanthalog Fumarate ViaSuspension Equilibration

Consistent with Example 1, tabernanthalog fumarate also was subjected tosuspension equilibration in various solvents. According to this examplecrystalline materials were observed from suspension stirring in varioussolvents. The materials were analyzed by proton NMR to confirm identity,stoichiometry and solvent content. Table 3 summarizes the crystallineforms identified using suspension equilibration.

TABLE 3 List of crystalline forms of tabernanthalog fumarate identifiedusing suspension equilibration. Solvent Content Conditions XRPD FIG.(via ¹H NMR) Stirred at 40° C. in 10 vol Pattern #2a FIG. 3 0.1% MeCNMeCN and 5 vol heptanes Stirred at 40° C. in 10 vol 2- Pattern #1 FIG. 4N.D MeTHF MeTHF and 5 vol heptanes Stirred at 40° C. in 10 volHemifumarate Pattern #21 FIG. 5 0.9 % IPA IPA and 5 vol heptanes Stirredat 20° C. in 10 vol Pattern #2b FIG. 8 4.0% EtOAc EtOAc and 5 volheptanes Stirred at 20° C. in 10 vol Pattern #8 FIG. 9 10% IPAc(isopropyl IPAc and 5 vol heptanes acetate) Stirred at 20° C. in 10 volPattern #4a FIG. 10 0.2% MeOH MeOH and 5 vol heptanes Stirred at 20° C.in 10 vol Pattern #4b FIG. 11 0.2% MeNO₂ MeNO₂ and 5 vol heptanesStirred at 20° C. in 10 vol Pattern #3 FIG. 12 5% Toluene Toluene and 5vol heptanes Stirred at 20° C. in 10 vol Pattern #6a FIG. 13 N.D. WaterWater and 5 vol heptanes

Example 4: Production of the Tabernanthalog Hemifumarate Salt

This example describes the production of tabernanthalog hemifumarate.Tabernanthalog free base and fumaric acid in equimolar amounts weredissolved methanol (10 vol) with heating, and the resultant solution wasconcentrated to dryness and the solid residue was analyzed by ¹H NMR,XRPD and DSC. The ¹H NMR spectrum for the hemifumarate product isprovided as FIG. 6 . This sample was subjected to equilibration in 20vol acetonitrile, dried and reanalyzed with XRPD, to provide crystallinetabernanthalog hemifumarate yielding the diffractogram provided in FIG.7 .

Example 5: Polymorph Screen of the Tabernanthalog Fumarate Salt

Abbreviations a^(w) Water activity AWS Analytical Working Standard ca.circa, approximately cf. to confer, to compare ° C. degree Celsius CPChemical Purity Da Dalton DSC Differential Scanning Calorimetry DTADifferential Thermal Analyses DVS Dynamic Vapour Sorption e.g. forexample etc. etcetera FaSSIF Fasted State Simulated Intestinal FluidFaSSGF Fasted State Simulated Gastric Fluid FeSSIF Fed State SimulatedIntestinal Fluid g gram GRAS Generally Recognized As Safe h hour HPLCHigh Performance Liquid Chromatography HSM Hot Stage Microscopy i.e.that is IR Infrared Spectroscopy IPC In Process Check J Joule KF KarlFischer (determination of the water content by coulometric titration) kgkilogram LOD Loss On Drying mAu milli-Absorption units (chromatographicunit of peak height) mAu * s milli-Absorption units multiplied by second(chromatographic unit of peak area) MET/CR Aptuit chromatography methodreference min. minute mg milligram ml millilitre mol mole, amount ofsubstance M.L Mother Liquors N/A Not Applicable n.a. not analyzed n.d.not detected nm nanometre NMR Nuclear Magnetic Resonance oab onanhydrous basis osfb on solvent free basis oasfb on anhydrous solventfree basis pH −log [H⁺] or pH = −log a_(H) ⁺ pK_(a) −log (K_(a)), aciddissociation constant PLM Polarized Light Microscopy REP Aptuit reportreference RFA Request for analysis (unique reference number) RB Roundbottom (referring to glassware) RH Relative Humidity (a_(w) * 100) RPReverse Phase RT Room Temperature (ambient, typically: 18 to 23° C.) ssecond T Temperature (° C.) TCNB 2,3,5,6-Tetrachloronitrobenzene(C₆HCl₄NO₂, F.W. 260.89 gmol⁻¹) TGA Thermogravimetric Analysis th.theoretical yield UV Ultra Violet vol. volume vs. versus v/vvolume/volume W Watt w/w weight/weight XRPD X-Ray Powder Diffraction

Definitions

Amorphous Exhibits no long-range crystal order and displays a diffusenoise halo x-ray diffraction pattern

Cross polarized light Light passed through two polaroid filtersorientated at ninety degrees to one another

Disordered The API lacks long range order and tends towards theamorphous phase. Crystalline substances are characterized bywell-defined XRPD reflections that occur because atoms are periodicallyarranged in space. When the API exhibits a reduction in long rangeperiodicity the X-rays are scattered in a greater number of directionsleading to less resolved and lowered intensity peaks. When thescattering occurs in many directions the structure is said to bedisordered or amorphous

Habit (crystal) Different crystal size or shape

Isostructural Contains many similarities to the crystal lattice of therelated single form

Isomorphic Retains the structural characteristics of the originallattice after dehydration or de-solvation and is usually metastable,e.g. a dehydrated non-stoichiometric hydrate; i.e. exhibits homomorphismusually generated via loss of solvent or water. The dehydrated latticeis usually disordered and physically unstable and can readily absorbmolecules of similar size and affinities to generate isomorphicsolvates.

Normal light Vibrates in all directions perpendicular to the axis towhich the light travels

Particle size Normally expressed as a volume distribution,(semi-qualitative measurements may be performed by SEM.

Plane polarized light Light passed through a polaroid filter whichallows light vibrating in one plane to be transmitted.

Photomicrograph Image captured of a small object under magnificationthrough an optical microscope.

Polymorphism Crystalline solid able to exhibit different crystallinephases.

Pseudopolymorphism Different crystal structure attributed to theincorporation of molecular water or solvent

Stoichiometric solvate Contains a fixed ratio of solvent that isintegral to the crystal structure

Non-stoichiometric solvate Contains a non-fixed ratio of solvent thatoccupies various structural voids. The crystal structure is retainedeven as the solvent ratio varies

Thermogram Differential scanning calorimetry trace: heat flow ony-ordinate (mW), time (minutes)/temperature (° C.) on x-ordinate.

A. Study Overview

This study summarizes the data collected from the polymorph screen thatwas performed on the tabernanthalog monofumarate salt.

Tabernanthalog monofumarate was supplied as crystalline solid (suppliedbatch, Pattern #1) and stoichiometry in the supplied batch, is 1.0 to1.0 by ¹H NMR. Fumaric acid is a 1,4-dicarboxylic acid and ismono-salified; hence, the tabernanthalog monofumarate salt as supplied,is a hydrogen fumarate acid salt. There was a risk that thetabernanthalog monofumarate salt may reproportionate into Tabernanthaloghemifumarate salt+0.5 fumaric acid; or disproportionate into discretenon-ionized entities, i.e., Tabernanthalog (native) and fumaric acid.Any manufacturing crystallization must involve complete dissolution ofeach precursor, otherwise there is a risk that regions of thetabernanthalog monofumarate salt, Tabernanthalog hemifumarate salt,non-ionized Tabernanthalog and non-ionized fumaric acid may occur in thesolid phase. Chemically, the azepine ring system of Tabernanthalog, isincapable of Michael addition to the fumaric acid counter ion.Esterification of the fumaric acid counterion by several alcohols ispossible (this was monitored by ¹H NMR).

B. Objectives

The objectives of this study were (a) to survey the experimentalpolymorph space of the tabernanthalog monofumarate salt, (b) identifyand characterize single anhydrous forms, and (c) determine thesuccession of these forms and nominate a preferred form that is suitablefor manufacturing scale-up.

C. Experimental

Instrumentation

i. DSC

A Mettler Toledo DSC 3 instrument was used for the thermal analysisoperating with STARe™ software. The analysis was conducted in 40 μl openaluminum pans, under nitrogen and sample sizes ranged from 1 to 10 mg.Typical analysis method was 20 to 250° C. at 10° C./minute.

Alternatively, a Mettler Toledo DSC 821 instrument was used for thethermal analysis operating with STARe™ software. The analysis wasconducted in 40 μl open aluminum pans, under nitrogen and sample sizesranged from 1 to 10 mg. Typical analysis method was 20 to 250° C. at 10°C./minute.

ii. FT-IR

FT-IR Spectra were acquired using a PerkinElmer Frontier FT-IRspectrometer. Samples were analyzed directly using a universal ATRattachment in the Mid and Far frequency ranges; 4000 to 30 cm⁻¹. Spectrawere processed using Spectrum software. Standard KBr windows are usedfor mid-IR applications; polyethylene and polyethylene/diamond windowsare used for operation in the far-IR. Further capabilities of theinstrument include a liquid flow cell with ZnSe windows used for rapidmonitoring of reactions. This couples with timebase software whichallows time-resolved measurements to be taken.

iii. LC-MS Routine Liquid Chromatography-Mass Spectrometry (LC-MS) datawere collected using the Agilent 1260 Infinity II interfaced with 1260Infinity II DAD HS and Agilent series 1260 Infinity II binary pump.

The instrument used a single quadrupole InfinityLab MSD. The instrumentwas calibrated up to 2000 Da.

iv. ¹H NMR

¹H NMR Spectra were acquired using a Bruker 400 MHz spectrometer anddata was processed using Topspin. Samples were prepared in DMSO-d₆ attypical concentrations of 10 to 20 mg/mL and up to 50 mg/mL for ¹H NMRw/w assay and calibrated to the corresponding non-deuterated solventresidual at 2.50 ppm.

v. ¹H NMR w/w Assay Assays (w/w) of API by ¹H NMR spectroscopy weremeasured by the project chemist.

Internal standard 2,3,5,6-terachloronitrobenzene (TCNB), (ca. 20 mg,F.W. 260.89) were dissolved in DMSO-d₆ (2.0 mL) and the ¹H NMR spectrumwas acquired using an extended relaxation method.

vi. Thermal Gravimetric Analysis

A Mettler Toledo TGA 2 instrument was used to measure the weight loss asa function of temperature from 25 to 500° C. The scan rate was typically5 or 10° C. per minute. Experiments and analysis were carried out usingthe STARe™ software. The analysis was conducted in 100 μL open aluminumpans, under nitrogen and sample sizes ranged from 1 to 10 mg.

vii. XRPD Analysis

X-Ray powder diffraction (XRPD) analysis was carried out using a BrukerD2 Phaser powder diffractometer equipped with a LynxEye detector. Thespecimens underwent minimum preparation but, if necessary, they werelightly milled in a pestle and mortar before acquisition. The specimenswere located at the center of a silicon sample holder within a 5 mmpocket (ca. 5 to 10 mg).

The samples were continuously spun during data collection and scannedusing a step size of 0.02° 2-theta (2θ) between the range of 4° to 40°2-theta. Data was acquired using either 3- or 20-minutes acquisitionmethods. Data was processed using Bruker Diffrac.Suite.

Peak tables report only peaks >10%.

Relative intensity values in peak tables were calculated using the Net.intensity values.

Background curvature is automatically calculated over 4 to 40° 2-thetaby the Brucker EVA software.

viii. HPLC (MET/CR/2616)

HPLC data was acquired using an Agilent HPLC instrument. Samples werediluted to 1 mg/mL concentration in H₂O/DMSO (1/1, v/v).

Method Parameters:

-   Column: Halo C18, 150×4.6 mm, 2.7 μm-   Inj. volume: 5 μL-   Detection: UV @212 nm-   Mobile Phase A: 0.1% TFA in water/acetonitrile 95/5 v/v-   Mobile Phase B: 0.05% TFA in water/acetonitrile 5/95 v/v

Time % A % B 0.0 100 0 2.0 100 0 25.0 50 50 30.0 0 100 32.0 0 100 32.1100 0 37.0 100 0

-   Flow rate: 1 mL/min-   Column temperature: 30° C.-   Run time: 37 minutes-   Integration time: 32 minutes-   Wash vial or syringe wash: Sample diluent

ix. DVS

The moisture sorption properties of the feed API were analyzed by DVSIntrinsic instrument (Surface Measurement System). Approximately 20 to50 mg of API was weighed onto an aluminum pan and loaded into theinstrument equilibrated at 25° C. The sample was equilibrated under adry atmosphere (0% relative humidity) for 60 minutes, before increasingthe humidity from 0% to 30% at 5% step increment and from 30% to 90% at10% step increment. A desorption cycle was also applied from 90% to 30%(10% step decrement) and from 30% to 0% (5% step decrement). A rate ofchange in mass per time unit (dm/dt) of 0.002%/min was set as theequilibrium parameter. Kinetic and isotherm graphs were calculated.

x. Solvents

Twenty-one solvents were selected for the polymorph screen and includedthe majority of ICH listed Class 3 (Table 4).

TABLE 4 Solvents used in the solubility screen ICH Solvents b.p. (° C.)Classes Acetone 56 3 Acetonitrile 82 2 tert-Butylmethyl 55 3 etherDichloromethane 40 2 DMSO Ethanol 78 3 Ethyl acetate 75 3 2-Propanol 833 iPrOAc 87 3 Methanol 65 2 Methylethyl ketone 80 3 2-Methyl THF 80 #Tetrahydrofuran 66 2 Toluene 111 2 Water 100 #

D. Polymorph Screen

i. Qualitative Solubility Screen (Experiment Reference 1)

a. Experimental Procedure

The tabernanthalog monofumarate salt (Pattern #1, Sample Reference 1, 25mg, 1 wt) was weighed out in 20 separate vials to qualitatively examinethe solubility in an array of diverse solvents. The solubility wastested initially at 5 vol at 20° C., 40° C. and reflux. If insoluble at5 vol, the solvent quantity was increased to 10 vol, 15 vol and 20 volof the respective solvent. The suspensions that occurred upon coolingdown (vials that did not show precipitation at 20° C., were subjected tosub-ambient temperatures) were centrifuged and the solvent wet pelletswere analyzed by XRPD. The insoluble suspensions were additionallyworked up for XRPD analysis. The resultant powder patterns weresubsequently cross-referenced against the input supplied material.

A summary of the experimental conditions and the findings is provided inTable 5.

TABLE 5 Summary of findings from solubility assessment* Experi- mentRefer- ence- 5 vol 10 vol 15 vol Sample ICH Solution at Solid onSolution at Solid on Solution at Solid on Reference Solvent Class 20° C.40° C. reflux cooling 20° C. 40° C. reflux cooling 20° C. 40° C. refluxcooling 1-A1 Acetone 3 X X X — X X X — X X X — 1-B1 MeCN 2 X X X — X X X— X X X — 1-C1 Butanol 3 X X X — X X Partial Yes X X ✓ Yes 1-D1 tBME 3 XX X — X X X — X X X — 1-E1 DCM 2 X X X — X X — — X X — — 1-F1 Et₂O 3 X XX — X X — — X X — — 1-G1 Ethanol 3 X X X — X X X — X Partial ✓ Yes 1-H1EtOAc 3 X X X — X X X — X X X — 1-I1 IPA 3 X X X — X X X — X X X — 1-J1iPrOAc 3 X X X — X X X — X X X — 1-K1 Methanol 2 X X ✓ Yes 1-L1 MEK 3 XX X — X X X — X X X — 1-M1 2-MeTHF 3 X X X — X X X — X X X — 1-N1 THF 2X X X — X X X — X X X — 1-O1 Toluene 2 X X X — X X X — X X X — 1-P1Water # X X ✓ Yes X Partial ✓ Yes 1-Q1 Dioxane 3 X X X — X X X — X X X —1-R1 CPME 3 X X X — X X X — X X X — 1-S1 Heptane 3 X X X — X X X — X X X— 1-T1 MIBK 3 X X X — X X X — X X X — 1-A1 Acetone 3 X X X — X X X — X XX — 1-B1 MeCN 2 X X X — X X X — X X X — 1-C1 Butanol 3 X X X — X XPartial Yes X X ✓ Yes 1-D1 tBME 3 X X X — X X X — X X X — 1-E1 DCM 2 X X— — X X — — X X — — 1-F1 Et₂O 3 X X — — X X — — X X — — 1-G1 Ethanol 3 XX X — X X X — X Partial ✓ Yes 1-H1 EtOAc 3 X X X — X X X — X X X — 1-I1IPA 3 X X X — X X X — X X X — 1-J1 iPrOAc 3 X X X — X X X — X X X — 1-K1Methanol 2 X X ✓ Yes 1-L1 MEK 3 X X X — X X X — X X X — 1-M1 2-MeTHF 3 XX X — X X X — X X X — 1-N1 THF 2 X X X — X X X — X X X — 1-O1 Toluene 2X X X — X X X — X X X — 1-P1 Water # X X ✓ Yes X Partial ✓ Yes 1-Q1Dioxane 3 X X X — X X X — X X X — 1-R1 CPME 3 X X X — X X X — X X X —1-S1 Heptane 3 X X X — X X X — X X X — 1-T1 MIBK 3 X X X — X X X — X X X— Experi- ment Refer- ence- 20 vol Sample ICH Solution Solid onReference Solvent Class 20° C. 40° C. reflux cooling 1-A1 Acetone 3 X XX — 1-B1 MeCN 2 X X X — 1-C1 Butanol 3 1-D1 tBME 3 X X X — 1-E1 DCM 2 XX — — 1-F1 Et₂O 3 X X — — 1-G1 Ethanol 3 X Partial ✓ Yes 1-H1 EtOAc 3 XX X — 1-I1 IPA 3 X X X — 1-J1 iPrOAc 3 X X X — 1-K1 Methanol 2 1-L1 MEK3 X X X — 1-M1 2-MeTHF 3 X X X — 1-N1 THF 2 X X X — 1-O1 Toluene 2 X X X— 1-P1 Water # 1-Q1 Dioxane 3 X X X — 1-R1 CPME 3 X X X — 1-S1 Heptane 3X X X — 1-T1 MIBK 3 X X X — 1-A1 Acetone 3 X X X — 1-B1 MeCN 2 X X X —1-C1 Butanol 3 1-D1 tBME 3 X X X — 1-E1 DCM 2 X X — — 1-F1 Et₂O 3 X X —— 1-G1 Ethanol 3 X Partial ✓ Yes 1-H1 EtOAc 3 X X X — 1-I1 IPA 3 X X X —1-J1 iPrOAc 3 X X X — 1-K1 Methanol 2 1-L1 MEK 3 X X X — 1-M1 2-MeTHF 3X X X — 1-N1 THF 2 X X X — 1-O1 Toluene 2 X X X — 1-P1 Water # 1-Q1Dioxane 3 X X X — 1-R1 CPME 3 X X X — 1-S1 Heptane 3 X X X — 1-T1 MIBK 3X X X — *The tabernanthalog fumarate salt was soluble in refluxingmethanol and water at 5 vol (200 mg / ml) and butanol at 15 vol (67 mg /ml).

b. Analytical Characterization Data

XRPD

The analytical characterization data of this study are provided in FIGS.16-33 and Tables 6-23.

TABLE 6 Peak angle data of 1-A1 (Experiment Reference 1-Sample ReferenceA1) (wet pellet, Pattern #12) 2-θ (°) d Value Rel. Intensity (%) 8.210.75 17 9.0 9.78 16 14.2 6.23 11 16.3 5.45 66 16.6 5.35 15 18.1 4.90 2218.2 4.86 14 18.8 4.73 11 19.3 4.60 14 20.2 4.39 24 21.4 4.14 24 22.33.99 12 22.9 3.88 17 25.1 3.55 13 25.5 3.49 100 26.1 3.41 13 26.8 3.3322 27.2 3.28 14

TABLE 7 Peak angle data of 1-B1 (Experiment Reference 1-Sample ReferenceB1) (wet pellet, Pattern #2a, Form B) 2-θ (°) d Value Rel. Intensity (%)9.1 9.74 28 12.2 7.22 13 14.2 6.22 13 15.6 5.67 19 16.0 5.52 13 16.35.42 82 17.1 5.19 38 17.4 5.09 12 18.1 4.91 22 18.8 4.71 10 20.6 4.30 1221.0 4.22 12 22.9 3.89 22 23.1 3.85 13 25.1 3.55 13 25.6 3.48 100 26.83.32 20 27.3 3.27 24

TABLE 8 Peak angle data of 1-C1 (Experiment Reference 1-Sample ReferenceC1) (wet pellet, Pattern #15) 2-θ (°) d Value Rel. Intensity (%) 8.510.44 36 9.0 9.82 23 9.5 9.31 28 10.6 8.36 14 11.1 7.98 19 16.3 5.43 10016.9 5.25 92 17.0 5.21 33 17.7 5.00 32 18.1 4.90 19 18.5 4.80 12 18.94.68 13 19.3 4.60 29 20.0 4.45 22 20.9 4.26 14 21.1 4.21 23 22.5 3.95 1723.4 3.80 44 24.2 3.67 10 24.5 3.63 68 25.0 3.56 16 25.2 3.53 25 25.63.48 63 26.3 3.38 18 26.8 3.32 14

TABLE 9 Peak angle data of 1-D1 (Experiment Reference 1-Sample ReferenceD1) (wet pellet, Pattern #1) 2-θ (°) d Value Rel. Intensity (%) 9.0 9.7622 14.2 6.23 12 16.3 5.43 73 16.7 5.29 24 17.0 5.21 11 17.4 5.08 12 17.75.00 17 18.1 4.90 20 18.8 4.71 12 19.3 4.59 27 21.1 4.21 15 22.3 3.98 1523.2 3.83 15 25.1 3.54 14 25.5 3.49 100 26.8 3.32 21 27.2 3.27 17 30.02.98 10

TABLE 10 Peak angle data of 1-E1 (Experiment Reference 1-SampleReference E1) (wet pellet, Pattern #1) 2-θ (°) d Value Rel. Intensity(%) 9.1 9.76 18 14.2 6.22 11 16.3 5.43 84 16.7 5.30 23 18.1 4.91 19 19.34.60 32 21.3 4.17 16 21.8 4.07 19 22.3 3.98 16 23.1 3.84 12 23.8 3.74 1025.1 3.54 13 25.5 3.49 100 26.1 3.41 23 26.8 3.32 23 27.2 3.27 16 30.02.98 10

TABLE 11 Peak angle data of 1-G1 (Experiment Reference 1-SampleReference G1) (wet pellet, Pattern #5) 2-θ (°) d Value Rel. Intensity(%) 8.3 10.70 100 11.1 7.97 11 15.4 5.74 11 17.0 5.21 19 21.5 4.13 1121.5 4.13 11

TABLE 12 Peak angle data of 1-H1 (Experiment Reference 1-SampleReference H1) (wet pellet, Pattern #9) 2-θ (º) d Value Rel. Intensity(%)  7.9 11.15  22  9.1 9.71 28 10.4 8.48 11 14.3 6.20 14 15.9 5.59 5716.4 5.41 79 16.8 5.27 12 17.0 5.20 21 17.5 5.06 10 18.1 4.89 24 18.94.69 11 19.4 4.57 29 20.7 4.29 14 21.8 4.07 20 22.3 3.98 16 24.6 3.61 4725.3 3.52 32 25.6 3.48 100  26.9 3.32 24 27.3 3.27 13 28.7 3.11 12

TABLE 13 Peak angle data of 1-I1 (Experiment Reference 1-SampleReference I1) (wet pellet, Pattern #10) 2-θ (º) d Value Rel. Intensity(%)  8.2 10.75  43  9.1 9.72 33 10.8 8.15 32 14.3 6.20 17 15.2 5.81 4016.4 5.41 84 16.9 5.24 100  18.1 4.90 18 19.2 4.62 20 19.8 4.47 34 21.44.15 57 21.8 4.07 19 22.2 4.00 24 22.6 3.93 14 23.5 3.78 55 23.7 3.75 2325.2 3.53 17 25.6 3.48 91 26.8 3.32 25 29.8 3.00 12 30.0 2.98 11

TABLE 14 Peak angle data of 1-J1 (Experiment Reference 1-SampleReference J1) (wet pellet, Pattern #8) 2-θ (º) d Value Rel. Intensity(%)  7.6 11.66  34  9.0 9.78 22 14.2 6.23 14 15.8 5.59 67 16.3 5.43 8516.7 5.32 12 17.4 5.08 10 18.1 4.91 26 18.8 4.71 11 19.1 4.64 28 19.34.61 19 20.6 4.31 28 21.9 4.05 11 22.3 3.98 15 23.8 3.73 11 24.3 3.67 5325.0 3.56 12 25.1 3.54 17 25.5 3.49 100  26.8 3.32 21 27.2 3.27 18 29.92.98 12

TABLE 15 Peak angle data of 1-K1 (Experiment Reference 1-SampleReference K1) (wet pellet, Pattern #6b) 2-θ (º) d Value Rel. Intensity(%)  8.2 10.71  29 13.0 6.83 26 16.5 5.36 22 19.6 4.53 18 19.5 4.55 100 20.6 4.30 17 25.3 3.52 12 26.1 3.42 59

TABLE 16 Peak angle data of 1-L1 (Experiment Reference 1-SampleReference L1) (wet pellet, not assigned) 2-θ (º) d Value Rel. Intensity(%)  7.6 11.66  19  7.9 11.12  22  9.2 9.66 30 14.3 6.19 18 16.1 5.49 3316.4 5.39 86 16.8 5.27 15 17.5 5.06 14 18.2 4.87 24 19.5 4.55 21 21.24.20 13 22.1 4.02 11 22.4 3.96 19 22.6 3.93 12 23.3 3.82 13 23.4 3.80 1124.8 3.59 22 25.1 3.54 18 25.7 3.47 100  26.9 3.31 22 27.4 3.26 16

TABLE 17 Peak angle data of 1-M1 (Experiment Reference 1-SampleReference M1) (wet pellet, Pattern #7) 2-θ (º) d Value Rel. Intensity(%)  7.3 12.06  29  9.2 9.63 26 14.4 6.16 14 16.0 5.54 54 16.4 5.39 9216.8 5.26 23 17.6 5.04 11 18.2 4.86 24 19.5 4.56 31 19.9 4.46 19 20.94.26 15 21.4 4.15 30 21.4 4.16 31 22.5 3.95 21 23.3 3.82 11 25.0 3.56 2725.7 3.47 100  27.0 3.31 21 27.4 3.25 19 30.1 2.96 10

TABLE 18 Peak angle data of 1-N1 (Experiment Reference 1-SampleReference N1) (wet pellet, Pattern #11) 2-θ (º) d Value Rel. Intensity(%)  7.4 11.93  39  9.0 9.78 17 10.6 8.34 11 11.1 7.98 13 14.2 6.23 1116.0 5.55 94 16.3 5.44 61 17.2 5.14 24 18.0 4.91 16 20.2 4.39 66 20.74.28 24 20.8 4.26 16 21.5 4.14 67 22.6 3.93 19 23.7 3.75 22 23.9 3.72 1725.1 3.55 15 25.6 3.48 100  26.8 3.32 20

TABLE 19 Peak angle data of 1-O1 (Experiment Reference 1-SampleReference O1) (wet pellet, Pattern #1) 2-θ (º) d Value Rel. Intensity(%)  9.2 9.61 26 14.4 6.14 17 14.4 6.14 18 16.5 5.38 80 16.8 5.27 4817.6 5.04 12 18.2 4.86 24 18.9 4.68 19 19.4 4.56 25 20.3 4.38 21 22.43.97 29 22.7 3.92 14 25.3 3.51 19 25.7 3.46 100  26.2 3.40 24 26.9 3.3126 27.4 3.26 16

TABLE 20 Peak angle data of 1-P1 (Experiment Reference 1-SampleReference P1) (wet pellet, Pattern #2c) 2-θ (º) d Value Rel. Intensity(%)  9.1 9.73 62 14.2 6.23 14 16.3 5.44 44 17.4 5.09 14 18.0 4.92 1821.9 4.05 16 22.2 4.00 11 22.5 3.94 11 25.1 3.55 27 25.5 3.49 100  26.73.33 13 27.2 3.28 12

TABLE 21 Peak angle data of 1-R1 (Experiment Reference 1-SampleReference R1) (wet pellet, Pattern #1) 2-θ (º) d Value Rel. Intensity(%)  9.2 9.61 24 14.4 6.16 12 15.1 5.87 5 16.5 5.38 77 16.8 5.26 38 17.75.02 16 17.9 4.96 17 18.3 4.85 35 19.0 4.67 11 19.5 4.56 47 20.3 4.37 1321.4 4.16 10 22.4 3.96 30 23.3 3.82 15 25.7 3.47 100 26.3 3.39 18 27.03.30 24 27.4 3.25 27 30.1 2.96 12

TABLE 22 Peak angle data of 1-S1 (Experiment Reference 1-SampleReference S1) (wet pellet, Pattern #1) 2-θ (º) d Value Rel. Intensity(%)  9.2 9.63 24 14.4 6.16 10 16.5 5.38 76 16.8 5.27 36 17.6 5.03 1617.8 4.97 14 18.2 4.86 30 19.0 4.67 11 19.4 4.57 47 22.2 4.00 14 22.43.96 26 23.2 3.82 12 25.7 3.47 100  26.3 3.39 17 27.0 3.30 27 27.4 3.2627 30.1 2.97 10

TABLE 23 Peak angle data of 1-T1 (Experiment Reference 1-SampleReference T1) (wet pellet, Pattern #1) 2-θ (º) d Value Rel. Intensity(%)  9.2 9.61 22 14.4 6.16 14 14.3 6.19 13 16.4 5.39 100  16.9 5.25 2817.6 5.04 12 18.2 4.86 27 19.0 4.67 16 19.4 4.56 28 20.4 4.35 23 22.43.97 35 23.2 3.84 13 25.4 3.51 23 25.7 3.47 94 26.4 3.38 22 27.0 3.30 2727.4 3.26 17

c. Conclusion

From the initial findings, the tabernanthalog monofumarate salt appearedto be a strong solvator. Samples 1-C1 (crystallized from butanol), 1-G1(crystallized from ethanol), 1-K1 (crystallized from methanol) and 1-P1(crystallized from water), were reanalyzed after drying, to includeXRPD, TGA and ¹H NMR, and confirm that the forms are true anhydrouspolymorphs or solvated forms. The XRPD data collected are summarizedbelow:

-   -   Powder patterns of 1-E1 (different 21.8° 2θ), 1-D1, 1-O1, 1-R1,        1-S1, 1-T1 closely resembled the tabernanthalog monofumarate        salt (Sample Reference 1, refer to FIG. 34 ).    -   Powder patterns 1-L1 and 1-M1 were paired and resembled Sample        Reference 1, except many of the reflections were offset by 0.1        to 0.2° 2θ (refer to FIG. 35 ).    -   Powder pattern 1-A1, closely resembled Sample Reference 1,        except additional reflections were present at 8.3°, 10.7° and        21.5° 2θ (refer to FIG. 36 and FIG. 16 ).    -   Powder pattern 1-F1, closely resembled Sample Reference 1,        except additional reflections were present at 9.7°, 17.1° and        24.4° 2θ (refer to FIG. 36 and FIG. 373 ).    -   Reflections of powder pattern 1-P1 were closely aligned with        those of Sample Reference 1, except key reflections at 16.7°,        19.3° were absent (refer to FIG. 36 and FIG. 30 ). It is worth        mentioning that 100% water is often a poor crystallization        solvent because it exerts weak control on lipophilic impurities;        although water can serve as a polarity modifier in certain        binary compositions.    -   Powder pattern 1-B1, exhibited key reflection differences at        12.3°, 15.7°, 16.0°, 17.2°, 19.3°, 20.7° and 22.9° 2θ (refer to        FIG. 36 and FIG. 17 ).    -   Powder pattern 1-C1, appeared to be a mixture of Sample        Reference 1 and potentially a new form, that exhibited key        reflection differences 8.5°, 9.6°, 10.6°, 11.1°, 16.9°, 17.8°,        20.0°, 20.9, 23.8° and 24.5° (refer to FIG. 36 and FIG. 18 ).    -   Powder pattern 1-G1, exhibited significant preferred orientation        effects, with v. strong reflection at 8.3°, this made comparison        more difficult, the phase appeared to be a new form that        contained remnants of Sample Reference 1 (refer to FIG. 36 and        FIG. 21 ).    -   Powder pattern 1-K1, appeared to be a new stable form (refer to        FIG. 36 and FIG. 25 ). Methanol 5 vol, may be a suitable        crystallization solvent.    -   The remainder of the patterns exhibited differences.

ii. Stability Examination of Supplied Material at 40° C./75% RH(Experiment Reference 2)

a. Experimental Procedure

The tabernanthalog monofumarate salt (Pattern #1, Sample Reference 1,100 mg) was placed inside a wide-necked, open vial (suffix -A) Thetabernanthalog monofumarate salt (Pattern #1, Sample Reference 1, 100mg) was placed inside a wide-necked, open vial and then inside doublepolyethene bags (SPC/PK/0052), tied tightly with cable ties (suffix -B).Both samples were maintained under equilibrium humidity of 75% RH at 40°C. (chamber placed in a pre-heated oven) and monitored, initially athourly and then weekly time points.

b. Analytical Characterization Data

¹H NMR

The ¹H NMR spectrum of 2-A8 (Experiment Reference 2-Sample Reference A8)(t=5 w, open vial), spectrum was acquired in DMSO-d₆ and calibrated tothe non-deuterated solvent residual at 2.50 ppm (FIG. 37 ). The ¹H NMRspectrum of 2-B8 (Experiment Reference 2-Sample Reference B8) (t=5 w,double bagged open vial), spectrum was acquired in DMSO-d₆ andcalibrated to the non-deuterated solvent residual at 2.50 ppm (FIG. 38).

TGA

TGA profile of 2-A8 (Experiment Reference 2-Sample Reference A8) (t=5weeks), analysis was acquired at a ramp rate of +10° C./minute (FIG. 39). TGA profile of 2-B8 (Experiment Reference 2-Sample Reference B8) (t=5weeks), analysis was acquired at a ramp rate of +10° C./minute (FIG. 40).

DSC

DSC profile of 2-A8 (Experiment Reference 2-Sample Reference A8) (t=5weeks), analysis was acquired at a ramp rate of +10° C./minute (FIG. 41). DSC profile of 2-B8 (Experiment Reference 2-Sample Reference B8) (t=5weeks), analysis was acquired at a ramp rate of +10° C./minute (FIG. 42).

XRPD

XRPD diffractograms reported herein are for t=4 w and 5 w as no formchange was observed during the 5-week period. The XRPD profile of 2-A7(Experiment Reference 2-Sample Reference A7) (t=4 w) is presented inFIG. 43 and the peaks are listed in Table 24. The XRPD profile of 2-A8(Experiment Reference 2-Sample Reference A8) (t=5 w) is presented inFIG. 44 and the peaks are listed in Table 25. The XRPD profile of 2-B7(Experiment Reference 2-Sample Reference B7) (t=4 w) is presented inFIG. 45 and the peaks are listed in Table 26. The XRPD profile of 2-B8(Experiment Reference 2-Sample Reference B8) (t=5 w) is presented inFIG. 46 and the peaks are listed in Table 27.

TABLE 24 Peak angle data of 2-A7 (Experiment Reference 2-SampleReference A7) (t = 4 w) 2-θ (º) d Value Rel. Intensity (%)  6.7 13.15 13  9.1 9.76 24 14.2 6.22 12 16.3 5.42 73 16.7 5.30 39 17.5 5.07 10 17.75.00 15 18.1 4.89 26 19.3 4.59 52 20.2 4.39 12 22.3 3.98 23 22.5 3.95 1323.1 3.84 13 25.1 3.54 16 25.6 3.48 100  26.2 3.40 17 26.8 3.32 21 27.33.27 23

TABLE 25 Peak angle data of 2-A8 (Experiment Reference 2-SampleReference A8) (t = 5 w) 2-θ (º) d Value Rel. Intensity (%)  9.0 9.79 1514.2 6.24 10 16.3 5.44 68 16.6 5.32 41 17.4 5.08 12 17.6 5.02 16 18.14.90 24 19.3 4.61 52 20.1 4.41 11 21.1 4.21 11 22.3 3.99 28 23.1 3.85 1523.7 3.75 10 25.1 3.55 19 25.5 3.49 100  26.1 3.41 17 26.8 3.33 24 27.23.28 28 28.6 3.12 11 30.0 2.98 13

TABLE 26 Peak angle data of 2-B7 (Experiment Reference 2-SampleReference B7) (t = 4 w) 2-θ (º) d Value Rel. Intensity (%)  6.8 13.01 16  9.1 9.67 31 13.0 6.82 13 14.3 6.18 14 16.4 5.39 83 16.8 5.28 46 17.65.04 15 17.8 4.98 16 18.2 4.87 31 19.4 4.57 57 20.3 4.38 14 21.3 4.17 1122.2 4.01 10 22.4 3.96 25 22.6 3.93 12 23.2 3.82 15 25.3 3.52 18 25.63.47 100  26.2 3.39 16 26.9 3.31 22 27.3 3.26 25 30.1 2.97 11

TABLE 27 Peak angle data of 2-B8 (Experiment Reference 2-SampleReference B8) (t = 5 w) 2-θ (º) d Value Rel. Intensity (%) 6.7 13.13 129.1 9.75 25 11.5 7.69 3 14.2 6.22 11 16.3 5.42 75 16.7 5.31 41 17.5 5.0713 17.7 5.00 16 18.1 4.89 24 19.3 4.59 53 20.2 4.40 10 22.3 3.98 26 23.13.84 14 25.2 3.53 18 25.5 3.48 100 26.1 3.41 17 26.8 3.32 22 27.2 3.2726 30.0 2.97 13

HPLC

The HPLC profile of 2-A5 (Experiment Reference 2-Sample Reference A5)(t=2 w) FIG. 47 . The HPLC profile of 2-A6 (Experiment Reference2-Sample Reference A6) (t=3 w) is presented in FIG. 48 . The HPLCprofile of 2-A7 (Experiment Reference 2-Sample Reference A7) (t=4 w) ispresented in FIG. 49 . The HPLC profile of 2-A8 (Experiment Reference2-Sample Reference A8) (t=5 w) is presented in FIG. 50 . The HPLCprofile of 2-B5 (Experiment Reference 2-Sample Reference B5) (t=2 w) ispresented in FIG. 51 . The HPLC profile of 2-B6 (Experiment Reference2-Sample Reference B6) (t=3 w) is presented in FIG. 52 . The HPLCprofile of 2-B7 (Experiment Reference 2-Sample Reference B7) (t=4 w) ispresented in FIG. 53 . The HPLC profile of 2-B8 (Experiment Reference2-Sample Reference B8) (t=5 w) is presented in FIG. 54 .

Photography

The results of these experiments are provided in FIGS. 55-61 .

c. Conclusion

Two equal portions of the tabernanthalog monofumarate salt (Pattern #1,Sample Reference 1, 100 mg, CP 97.64% area) were weighed out; one ofwhich was placed inside an open vial, while the other was doublepolyethene bagged, each bag was tied tightly with cable ties. The areaof finely divided solid, exposed to the condition was the same acrossboth experiments. The experiment is performed to mimic a typicalpackaging configuration and monitor the stability of the materialdirectly exposed to the conditions, and the stability of the same amountwhen double-bagged. Both samples were maintained at 75% RH at 40° C. andmonitored by XRPD at time points t=1 h, 3 h, 24 h, 48 h, 7 d, 2 w, 3 w,4 w and 5 w.

Under the conditions evaluated during this study, all analyses wereconsistent with Pattern #1 of Reference Sample 1 (refer to FIG. 62 andFIG. 63 ), indicating that the tabernanthalog monofumarate salt isphysically and chemically stable under these conditions. HPLC(chromatography was performed using generic method) data collected didnot show significant changes in chemical purity, indicating goodstability of the phase under the conditions examined. Photographs werealso taken to observe any differences in appearance. 2-A became darkerduring its exposure to the humidity conditions.

TG analyses of the last timepoint collected from both experiments wereconsistent with the input with no significant water absorption (refer toFIG. 64 and FIG. 65 ). DSC analyses of the two absorbents werecomparable with the input. 2-A8 and 2-B8 exhibited a slightly largerendotherm event with onset 121° C. compared to Sample Reference 1(Pattern #1, refer to FIG. 66 and FIG. 67 ). The summary of HPLC datacollected during Experiment Reference 2 is provided in Table 28.

TABLE 28 Summary of HPLC data collected during Experiment Reference 2XRPD XRPD XRPD XRPD XRPD HPLC t = 3 h t = 24 h t = 48 h t = 7 days t = 2w HPLC Reference Conditions Input Batch (% area) (−A1, −B1) (−A2, −B2)(−A3, −B3) (−A4, −B4) (−A5, −B5) (% area) 2-A1 to Open- Tabern- 97.64Consistent Consistent Consistent Consistent Consistent 97.26 2-A8necked, anthalog with input with input with input with input with inputwide vial at fumarate batch of batch of batch of batch of batch of 75%(CAT8931) tabern- tabern- tabern- tabern- tabern- RH/40° C. for anthaloganthalog anthalog anthalog anthalog 5 weeks fumarate fumarate fumaratefumarate fumarate 2-B1 to Sealed Tabern- Consistent ConsistentConsistent Consistent Consistent 97.44 2-B8 PK0056 anthalog with inputwith input with input with input with input electrostatic fumarate batchof batch of batch of batch of batch of bags at 75% (CAT8931) tabern-tabern- tabern- tabern- tabern- RH/40° C. 5 anthalog anthalog anthaloganthalog anthalog weeks fumarate fumarate fumarate fumarate fumarateXRPD XRPD XRPD t = 3 w HPLC t = 4 w HPLC t = 5 w HPLC ReferenceConditions Input Batch (−A6, −B6) (% area) (−A7, −B7) (% area) (−A8,−B8) (% area) 2-A1 to Open- Tabern- Consistent 97.01 Consistent 97.98Consistent 97.34 2-A8 necked, anthalog with input with input with inputwide vial at fumarate batch of batch of batch of 75% (CAT8931) tabern-tabern- tabern- RH/40° C. for anthalog anthalog anthalog 5 weeksfumarate fumarate fumarate 2-B1 to Sealed Tabern- Consistent 97.02Consistent 98.38 Consistent 97.54 2-B8 PK0056 anthalog with input withinput with input electrostatic fumarate batch of batch of batch of bagsat 75% (CAT8931) tabern- tabern- tabern- RH/40° C. 5 anthalog anthaloganthalog weeks fumarate fumarate fumarate

iii. Thermal Examinations

a. Experimental Procedure

Described for the supplied (Sample Reference 1): The tabernanthalogmonofumarate salt (ca 10.0 mg, Pattern #1) was placed in an aluminumcrucible (40 μl) and heated at a rate of +10° C./min from 20 to 155° C.to capture the exothermic event that occurred ca 135 to 155° C. (FIG. 72). The crucible was removed from the instrument and allowed to cool to20° C. (<1 s), the specimen was expressed from the spent crucible andanalyzed by XRPD and compared with the starting material (refer to FIG.75 ).

b. Analytical Characterization Data

DSC

The DSC results are provided in FIGS. 68-70 .

XRPD

The XRD results are provided in FIG. 71 and Table 29.

TABLE 29 Peak angle data of the tabernanthalog monofumarate salt (SampleReference 1, Pattern #1) specimen from DSC crucible at ca. 150° C. 2-θ(º) d Value Rel. Intensity (%) 8.7 10.19 11 9.1 9.72 12 11.0 8.00 2312.1 7.28 12 12.6 7.03 15 14.1 6.28 17 15.5 5.70 25 16.0 5.52 96 16.35.45 45 16.8 5.29 14 18.0 4.93 86 18.9 4.69 20 19.3 4.60 16 20.9 4.24 1921.4 4.15 35 22.4 3.96 17 23.0 3.87 29 24.9 3.58 12 25.6 3.47 100 25.93.43 27 26.8 3.33 30

c. Conclusion

An initial thermocycle experiment was performed to identify the eventsduring a cycle from 20° C. to 200° C. at +10° C./min, from 200° C. to−20° C. at −20° C./min and −20° C. to 25° C. at +10° C./min (refer toFIG. 72 ). The abrupt change in c_(p) at the beginning of each thermalsegment was attributed to the weight difference between the referenceand sample pans. The shallow endotherm (36 to 101° C.) is ambiguous andmay be drying of surface moisture/release of weakly bound water, thetransition approximately coincided with TG-Δ wt. −2.1% w/w, (72 to 122°C., refer to FIG. 299 ). This was confirmed via simultaneous TGA/DSC(FIG. 73 ).

At first glance, the 2^(nd) endotherm (onset 121° C.), appeared to be amelt, followed by shouldered exotherm (onset 140° C.), which maycorrespond to crystallization; whether these events extend across theentire bulk phase are not known.

The molten specimen did not recrystallize into the same form on cooling.Unlikely that disproportionation occurred on heating (m.p. non-ionizedFu ac 287° C.).

At higher resolution, the shallow endotherm (36 to 101° C.) would seemto be associated with non-crystal-bonded volatile release, presumablywater [−Δ wt. −1.9% w/w, (up to 120° C.)]. The 2^(nd) endotherm (onset121° C.) is also associated with volatile release, presumably water(−0.5% w/w), or perhaps water and acetonitrile (−0.3+−0.2% w/w), FIG. 73. We can surmise that these volatiles (−0.5% w/w) are probablycrystal-bonded, since the exotherm that followed at ca 140° C., mostlikely corresponded to significant structural re-organization (modulatedDSC to impart better granularity to this event is reported (FIG. 74 ).

With modulated DSC, the proposed crystallization events (138° C.) wereslightly better resolved; however, it was still shouldered (refer toFIG. 74 ). Therefore, the simple melt-crystallization explanation (120to 160° C.) given on FIG. 73 is not quite true and now appears toconsist of volatile release and endothermic transition (melt), followedby exothermic transition (crystallization, refer to FIG. 74 ) andbimodal endotherm.

Following the data collected above, XRPD analysis was performed on thespecimen that was heated at ca. 155° C. (refer to yellow circle in FIG.72 ) in an aluminum DSC crucible (FIG. 70 ).

The specimen was withdrawn slightly prematurely, nevertheless, based onXRPD diffractogram overlay with the input (FIG. 75 ), we can concludethat the exo. event ca 135 to 155° C., corresponded to structuralre-organization (crystallization).

iv. DVS Analyses (Experiment Reference 4)

a. Experimental Procedure

The moisture sorption properties of the feed API (active pharmaceuticalingredient) were analyzed by DVS Intrinsic instrument (SurfaceMeasurement System). Approximately 20 to 50 mg of API was weighed ontoan aluminum pan and loaded into the instrument equilibrated at 25° C.The sample was equilibrated under a dry atmosphere (0% relativehumidity) for 60 minutes, before increasing the humidity from 0% to 30%at 5% step increment and from 30% to 90% at 10% step increment. Adesorption cycle was also applied from 90% to 30% (10% step decrement)and from 30% to 0% (5% step decrement). A rate of change in mass pertime unit (dm/dt) of 0.002%/min was set as the equilibrium parameter.Kinetic and isotherm graphs were calculated.

It is noted that 4-A4 (Experiment Reference 4-Sample Reference A4) and8-A4 (Experiment Reference 8-Sample Reference A4) are identical.Furthermore, 4-A2 (Experiment Reference 4-Sample Reference A2) and 8-A2(Experiment Reference 8-Sample Reference A2) are identical.

b. Analytical Characterization Data

DVS

DVS data of Sample Reference 1 is provided in FIG. 76 . The massequilibrated DVS data of Sample Reference 1 is provided in FIG. 77 .Mass equilibrated DVS data of tabernanthalog monofumarate salt (Pattern#1, supplied material 4-A4 (Experiment Reference 4-Sample Reference A4)(Form A) is provided in FIG. 78 .

XRPD

The XRPD profile of Sample Reference 1 post DVS (Mass equilibrated DVS)is provided in FIG. 79 and the list of peaks are provided in Table 30.

The XRPD overlay of the tabernanthalog monofumarate salt (SampleReference 1, pattern #1, black) post DVS (red, Pattern #1) is providedin FIG. 80 . The XRPD profile of 4-A4 (Experiment Reference 4-SampleReference A4) post DVS (Mass equilibrated DVS, Pattern #6a) is providedin FIG. 81 and the peak listing is provided in Table 31.

TABLE 30 Peak angle data of Sample Reference 1 post DVS (Pattern #1) 2-θ(º) d Value Rel. Intensity (%) 6.7 13.10 15 9.1 9.73 30 12.9 6.85 1014.3 6.21 14 16.4 5.41 80 16.7 5.30 48 17.5 5.06 14 17.7 5.00 16 18.14.88 29 18.9 4.70 11 19.3 4.59 54 20.2 4.39 13 21.2 4.19 13 22.4 3.97 2622.5 3.94 10 23.2 3.84 14 25.2 3.53 17 25.6 3.48 100 26.2 3.40 14 26.83.32 22 27.3 3.27 26 30.0 2.97 10

TABLE 31 Peak angle data of 4-A4 (Experiment Reference 4-SampleReference A4) post DVS (Pattern #6a) 2-θ (º) d Value Rel. Intensity (%)12.9 6.84 11 16.5 5.36 89 19.5 4.54 100 20.6 4.30 80 22.0 4.03 20 25.33.52 77 26.1 3.42 32 33.5 2.67 12 37.8 2.38 11

c. Conclusion

There are two main methods, one is by time where the equilibration isgiven by a fixed time, i.e., 1 hour per step. The second one is by massper time unit (dm/dt) of 0.0020%/min, that is when the difference inweight is less than 0.00200 the instrument moves onto the next step. Forunknown hygroscopicity, the method by time is indicated because it givesan idea of water affinity. Ideally the analysis is repeated using themass equilibration method to confirm. By experience for hygroscopicsamples, the analysis can continue for days. For non-hygroscopic samplesthe difference between the two methods may not be significant.

DVS Isotherm plot of the tabernanthalog monofumarate salt (SampleReference 1, Pattern #1) obtained with 0 to 90% to 0% RH vs time isprovided in FIG. 82 . Mass equilibrated DVS Isotherm plot of thetabernanthalog fumarate salt (Sample Reference 1) obtained with 0 to 90%to 0% RH is provided in FIG. 83 . Mass equilibrated DVS Isotherm plot ofthe tabernanthalog fumarate salt (4-A4) obtained with 0 to 90% to 0% RHis provided in FIG. 84 .

Consequently, supplied batch Sample Reference 1 was initially analyzedby the fixed time method (FIG. 82 ) and subsequently by mass per timeunit (dm/dt) of 0.002%/min (FIG. 83 ) and once the stable form wasgenerated (4-A2) (Experiment Reference 4-Sample Reference A2, Pattern#6a, Form A) the analysis was repeated is by mass per time unit (dm/dt)of 0.002%/min (FIG. 84 ). The sample exhibited hygroscopic isotherm withnegligible hysteresis.

v. Re-Proportionation Examination (Experiment Reference 5)

a. Experimental Procedure

Equimolar quantities Tabernanthalog (native) (TBG Native, 25.6 mg) andthe tabernanthalog monofumarate salt (Pattern #1, Sample Reference 1,37.9 mg) were dissolved in methanol (1 ml, 20 vol) at reflux and theresultant solution was dried to a residue (5-01) (Experiment Reference5-Sample Reference 01) under nitrogen flow. ¹H NMR spectroscopy (FIG. 85), to confirm the formation of the tabernanthalog hemifumarate.

Exyt. #1: Tabernanthalog hemifumarate (5-01) (Experiment Reference5-Sample Reference 01) was equilibrated in acetonitrile at 20° C. andsampled at time points 20 h to determine if the hemi-salt (Experiment2-03) is metastable with respect to the unary salt and reverts to thetabernanthalog monofumarate salt under suspension equilibrationconditions (i.e. 2 Tabernanthalog hemifumarate →Tabernanthalogmonofumarate salt+Tabernanthalog (native)).

Exyt. #2: an equi-weight mixture of tabernanthalog hemifuumarate(Pattern #14, 5-B3) (Expt. #2 of Experiment Reference 5-Sample ReferenceB3) and the tabernanthalog monofumarate salt (Pattern 1, ReferenceNumber 1, 23.6 mg) were competitively equilibrated in acetonitrile at20° C. (5-B4; Experiment Reference 5-Sample Reference B4) and 40° C.(5-B5; Experiment Reference 5-Sample Reference B5). The output wasanalyzed by XRPD (FIG. 94 ).

On a separate note, the hemi-salt preparation was repeated by dissolvingTabernanthalog (native) (TBG Native, 50.6 mg) and fumaric acid (10.3 mg,0.5 equiv) in methanol (1 ml, 20 vol), as more material was required for5-B4 (Experiment Reference 5-Sample Reference B4).

b. Analytical Characterization Data

¹H NMR

¹H NMR spectrum of (5-01) (Experiment Reference 5-Sample Reference 01)was acquired in DMSO-d₆ and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 0.5 (FIG. 85 ). ¹H NMRspectrum of 5-B1 (Experiment Reference 5-Sample Reference B1) wasacquired in DMSO-d₆ and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 0.5 (FIG. 86 ). ¹H NMRspectrum of 5-B3 was acquired in DMSO-d₆ and calibrated to thenon-deuterated solvent residual at 2.50 ppm API to Fumaric acid, 1.0 to0.5. Residual solvents: MeOH: 2.4% w/w, MeCN: 0.3% w/w (acetone detectedderived from NMR tube, as it was not used in the process: 0.2% w/w)(FIG. 86A). ¹H NMR spectrum of 5-B5 (Experiment Reference 5-SampleReference B5) was acquired in DMSO-d6 and calibrated to thenon-deuterated solvent residual at 2.50 ppm API to Fumaric acid, 1.0 to0.5 (FIG. 87 ).

DSC

DSC profile of 5-B3 (Experiment Reference 5-Sample Reference B3),analysis was acquired at a ramp rate of +10° C./minute (FIG. 87A).

DSC profile of 5-B5 (Experiment Reference 5-Sample Reference B5),analysis was acquired at a ramp rate of +10° C./minute (FIG. 88 ).

XRPD

XRPD profile of 5-B2 (Tabernanthalog·0.5 Fumarate; Experiment Reference5-Sample Reference B2) is presented in FIG. 89 and the peak angle datais provided in Table 32. XRPD profile of 5-B3 (Experiment Reference5-Sample Reference B3) is presented in FIG. 89A and the peak angle datais provided in Table 32A.

XRPD profile of 5-B4 (Experiment Reference 5-Sample Reference B4) ispresented in FIG. 90 and the peak angle data is provided in Table 33.XRPD profile of 5-B5 (Experiment Reference 5-Sample Reference B5) ispresented in FIG. 91 and the peak angle data is provided in Table 34.

TABLE 32 Peak angle data of 5-B2 (Tabernanthalog · 0.5Fumarate;Experiment Reference 5- Sample Reference B2) 2-θ (º) d Value Rel.Intensity (%) 8.2 10.78 66 11.3 7.84 91 12.8 6.89 16 15.5 5.71 74 17.05.23 100 17.8 4.97 15 18.0 4.91 15 19.0 4.67 17 18.9 4.70 18 19.4 4.5716 20.2 4.40 90 21.4 4.15 89 22.6 3.93 74 23.6 3.77 90 24.2 3.67 43 24.73.60 40 25.9 3.44 20 27.1 3.29 20 30.2 2.96 21 30.7 2.91 37 34.4 2.61 12

TABLE 32A Peak angle data of 5-B3 (Experiment Reference 5-SampleReference B3) 8.2 10.79 100 11.2 7.902 36 12.8 6.93 10 15.5 5.70 56 17.05.21 54 18.1 4.91 18 18.4 4.83 13 19.2 4.61 17 19.4 4.56 13 20.2 4.39 4421.3 4.17 13 21.5 4.13 29 22.6 3.93 51 23.7 3.75 32 24.3 3.67 17 24.83.59 31

TABLE 33 Peak angle data of 5-B4 (Experiment Reference 5- SampleReference B4) 2-θ (º) d Value Rel. Intensity (%) 4.3 20.31 100 8.7 10.1512 13.1 6.77 29 14.5 6.12 68 16.2 5.46 10 16.9 5.25 22 17.5 5.08 94 18.74.74 55 19.3 4.59 81 20.1 4.42 71 21.0 4.23 64 21.8 4.07 17 23.3 3.81 4323.7 3.75 62 24.8 3.59 16 26.8 3.33 14 27.5 3.24 34 28.0 3.18 23 29.13.07 13 29.2 3.06 11 29.7 3.01 27 30.8 2.90 13 31.8 2.81 36 33.3 2.69 1135.0 2.56 13 36.1 2.48 13 37.6 2.39 12 38.9 2.31 31

TABLE 34 Peak angle data of 5-B5 (Experiment Reference 5- SampleReference B5) 2-θ (º) d Value Rel. Intensity (%) 12.2 7.27 11 15.5 5.7141 15.8 5.62 21 16.2 5.47 42 16.9 5.24 100 20.5 4.32 46 20.8 4.26 3821.4 4.16 24 22.7 3.91 69 24.7 3.61 40 25.4 3.50 93 26.6 3.34 22 27.23.28 66 28.2 3.17 15 28.5 3.13 16 29.8 2.99 11 31.9 2.80 13

LC-MS

LC-MS report of (5-01) (Experiment Reference 5-Sample Reference 01) isprovided in FIG. 92 .

c. Conclusion

Expt. #1: at the 20 h time point, tabernanthalog hemifumarate, did notre-proportionate into the tabernanthalog monofumarate salt and fumaricacid; the output was consistent with tabernanthalog hemifumarate (FIG.93 ).

Expt. #2: stirred for 48 h at 20° C. and 18 h at 40° C.; during thistime the powder diffraction pattern of the product began to resemblePattern #19 (a unary fumarate; 7-A1; Experiment Reference 7-SampleReference A1); hence re-proportionation into the unary-fumarate appearedto be favored over the hemi-fumarate, under competitive suspensionequilibration conditions (FIG. 94 ). Therefore, if regions oftabernanthalog hemifumarate are generated during the production of thetabernanthalog monofumarate salt, the former would be expected to revertto the latter during the ageing cycle.

vi. Suspension Equilibration at 20° C. (Experiment Reference 6) and 40°C. (Experiment Reference 7)

a. Experimental Procedure

Separate portions of the tabernanthalog monofumarate salt (SampleReference 1, Pattern #1, ca 50 mg, 1.0 wt.) were charged to separatevessels. The appropriate solvents (e.g. 250 μl, 5.0 vol), were chargedto the vessels and the mixtures were stirred for several days at theirrelevant temperatures e.g. 20 and 40° C. After this time the productswere cooled, isolated by centrifugation, analyzed as wet pellet(suffix-1) by XRPD and dried under reduced pressure at 40° C. (suffix-2)and re-analyzed by XRPD and companion analyses for evidence ofalternative crystalline forms.

b. Analytical Characterization Data

Suspension equilibration is a thermodynamic dwelling technique, designedto promote the evolution of the API into a more stable phase. Thetabernanthalog monofumarate salt (Sample Reference 1, Pattern #1) wassubjected to this technique at ambient temperature (20° C., Table 35)and at elevated temperature (40° C., Table 36), in a diverse range ofsolvents. The primary aim is to identify a stable, anhydrous monotropicform that is suitable for future development.

The products were isolated by centrifugation and analyzed wet by XRPD.After drying, the samples were reanalyzed.

TABLE 35 Summary table of suspension equilibration at 20° C. ExperimentObser- Obser- Obser- Reference- Input Key chemical vations vationsvations XRPD XRPD Sample Input weight functional b.p. ICH (t = 0 (t = 1d t = 7 d (IPC, (post oven Reference reference (mg) Solvent groups (°C.) Classes @ 20° C.) @ 20° C.) @ 20° C.) 6 d, wet) dried) 6-ATabernanthalog• 50.0 Acetone Symmetrical  56 3 Suspension SuspensionSuspension Pattern Pattern Monofumarate ketone #12 #2b 6-B (CAT8931)50.2 Acetonitrile Simple dipolar-  82 2 Suspension Suspension SuspensionPattern Pattern aprotic nitrile #1 #1 6-C 50.0 tert-Butyl- Branched  553 Suspension Suspension Suspension Pattern Pattern methyl aliphatic #1#1 ether methoxy ether 6-D 50.7 Chloro- Aromatic halide 131 2 SuspensionSuspension Suspension Pattern Pattern benzene #3 #3 6-E 50.1 Dichloro-Chlorinated  40 2 Suspension Suspension Suspension Pattern Patternmethane hydrocarbon #4b #4b 6-F 50.8 Ethanol Linear aliphatic  78 3Suspension Suspension Suspension Pattern Pattern alcohol #5 #4a 6-G 50.4Ethyl Aliphatic ester  75 3 Suspension Suspension Suspension PatternPattern acetate #9 #2b 6-H 50.1 Ethyl Aldehyde  54 3 SuspensionSuspension Suspension Pattern Pattern formate aliphatic ester #2d #2b6-I 50.4 Heptane Linear alkane  98 3 Suspension Suspension SuspensionPattern Pattern #1 #1 6-J 50.0 Isopropyl Branched  87 3 SuspensionSuspension Suspension Pattern Pattern acetate aliphatic ester #8 #8 6-K50.1 Methanol Simple aliphatic  65 2 Suspension Suspension SuspensionPattern Pattern alcohol #4a #4a 6-L 50.8 Methyl Simple aliphatic  57 3Suspension Suspension Suspension Pattern Pattern acetate ester #13 #2b6-M 50.0 Methylethyl Asymmetric  80 3 Suspension Suspension SuspensionPattern Pattern ketone dialkyl ketone #1 #1 6-N 50.4 2-Methyl Asymmetric 80 # Suspension Suspension Suspension Pattern Pattern THF cyclic ether#7 #1 6-O 50.1 Nitro- Dipolar aprotic 100 2 Suspension SuspensionSuspension Pattern Pattern methane nitro #1 #4b 6-P 50.4 2-PropanolBranched  83 3 Suspension Suspension Suspension Pattern Patternaliphatic #10 #4a alcohol 6-Q 50.3 Tetrahydro- Symmetric  66 2Suspension Suspension Suspension Pattern Pattern furan cyclic ether #11#2b 6-R 50.2 Toluene Alkyl aromatic 111 2 Suspension SuspensionSuspension Pattern Pattern hydrocarbon #3 #3 6-S 50.7 Water Dihydrogen100 # Suspension Suspension Suspension Pattern Pattern oxide #6a #6a

TABLE 36 Summary table of suspension equilibration at 40° C. ExperimentObser- Obser- Obser- XRPD Reference- Input Key chemical vations vationsvations XRPD (post Sample Input weight functional b.p. ICH (t = 0 (t = 1d t = 7 d (6 d, oven Reference reference (mg) Solvent groups (° C.)Classes @ 40° C.) @ 40° C.) @ 40° C.) wet) dried) 7-A Tabernanthalog•50.0 Acetone Symmetrical  56 3 Suspension Suspension Suspension PatternPattern fumarate ketone #19 #19 7-B (CAT8931) 50.2 Acetonitrile Simpledipolar-  82 2 Suspension Suspension Suspension Pattern Pattern aproticnitrile #2a #2a 7-C 50.0 tert-Butyl- Branched  55 3 Suspension FeintSuspension Pattern Pattern methyl aliphatic suspension #1 #1 ethermethoxy ether 7-D 50.7 Chloro- Aromatic halide 131 2 SuspensionSuspension Suspension Pattern Pattern benzene #3 #1 7-E 50.1 Dichloro-Chlorinated  40 2 Suspension Suspension Suspension Not Pattern methanehydrocarbon analysed #1 7-F 50.8 Ethanol Linear  78 3 SuspensionSuspension Suspension Pattern Insuf- aliphatic #5 ficient alcoholmaterial 7-G 50.4 Ethyl Aliphatic ester  75 3 Suspension SuspensionSuspension Pattern Pattern acetate #9 #1 7-H 50.1 Ethyl Aldehyde  54 3Suspension Suspension Suspension Pattern Pattern formate aliphatic ester#2d #2b 7-I 50.4 Heptane Linear alkane  98 3 Suspension SuspensionSuspension Pattern Pattern #1 #1 7-J 50.0 Isopropyl Branched  87 3Suspension Suspension Suspension Pattern Pattern acetate aliphatic ester#2a #2a 7-K 50.1 Methanol Simple  65 2 Suspension Partial SuspensionInsuf- Insuf- aliphatic dissolution ficient ficient alcohol materialmaterial 7-L 50.8 Methyl Simple  57 3 Suspension Suspension SuspensionPattern Pattern acetate aliphatic ester #13 #1 7-M 50.0 MethylethylAsymmetric  80 3 Suspension Suspension Suspension Pattern Pattern ketonedialkyl ketone #2a #2a 7-N 50.4 2-Methyl Asymmetric  80 # SuspensionSuspension Suspension Pattern Pattern THF cyclic ether #7 #1 7-O 50.1Nitro- Dipolar 100 2 Suspension Suspension Suspension Pattern Patternmethane aprotic nitro #17 #2a 7-P 50.4 2-Propanol Branched  83 3Suspension Suspension Suspension Pattern Pattern aliphatic #10 #21alcohol 7-Q 50.3 Tetrahydro- Symmetric  66 2 Suspension Sticky SolidSuspension Pattern Insuf- furan cyclic ether #11 ficient material 7-R50.2 Toluene Alkyl aromatic 111 2 Suspension Suspension SuspensionPattern Insuf- hydrocarbon #1 ficient material 7-S 50.7 Water Dihydrogen100 # Suspension Partial Suspension Pattern Insuf- oxide dissolution #8ficient (amor- material phised)

XRPD

The XRPD data is provided in FIGS. 95-145 and Tables 37-87. XRPDdiffractograms not shown are reported on the characterization datasection.

TABLE 37 Peak angle data of 6-A2 (Experiment Reference 6- SampleReference A2) (Pattern#2b) 2-θ (º) d Value Rel. Intensity (%) 9.0 9.7827 14.2 6.24 12 15.5 5.69 16 16.3 5.44 82 17.4 5.09 17 18.0 4.91 28 18.84.72 14 22.3 3.98 21 22.5 3.95 23 24.7 3.60 17 25.0 3.56 21 25.5 3.49100 26.8 3.33 26

TABLE 38 Peak angle data of 6-B1 (Experiment Reference 6- SampleReference B1) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.8 13.0323 9.1 9.70 32 13.0 6.83 11 14.3 6.20 13 16.4 5.41 84 16.8 5.27 54 17.55.05 16 17.8 4.97 22 18.2 4.87 32 19.4 4.57 66 20.3 4.37 18 21.4 4.16 1422.3 3.97 23 22.4 3.97 27 23.2 3.83 17 25.3 3.51 25 25.6 3.48 100 26.33.39 19 26.9 3.31 20 27.3 3.26 27

TABLE 39 Peak angle data of 6-B2 (Experiment Reference 6- SampleReference B2) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.7 13.1416 9.1 9.75 22 12.9 6.86 10 14.2 6.22 11 16.3 5.43 69 16.7 5.29 45 17.55.07 14 17.8 4.99 20 18.1 4.89 27 19.3 4.59 58 20.2 4.39 15 21.3 4.17 1222.3 3.98 27 23.1 3.84 16 25.5 3.48 100 26.2 3.40 17 26.8 3.32 20 27.23.27 26

TABLE 40 Peak angle data of 6-C1 (Experiment Reference 6- SampleReference C1) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.8 12.9315 9.2 9.63 23 13.0 6.81 10 14.3 6.17 11 16.4 5.39 72 16.9 5.25 44 17.65.02 20 17.9 4.94 23 18.2 4.86 34 19.4 4.56 56 20.3 4.37 12 21.4 4.15 1122.5 3.96 28 23.3 3.82 14 25.7 3.47 100 26.3 3.38 20 27.0 3.29 25 27.33.26 27

TABLE 41 Peak angle data of 6-C2 (Experiment Reference 6- SampleReferenceC2) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.7 13.1117 9.1 9.74 30 12.9 6.85 12 14.3 6.21 13 16.3 5.42 84 16.8 5.28 52 17.55.06 16 17.8 4.98 24 18.2 4.88 32 18.9 4.70 10 19.3 4.59 59 20.2 4.39 1421.3 4.17 13 22.3 3.98 28 22.5 3.94 11 23.1 3.84 14 25.4 3.51 39 25.63.48 100 26.2 3.40 19 26.9 3.32 23 27.3 3.27 25

TABLE 42 Peak angle data of 6-D1 (Experiment Reference 6- SampleReference D1) (Pattern #3) 2-θ (º) d Value Rel. Intensity (%) 8.5 10.4234 9.1 9.71 53 9.8 9.03 16 11.3 7.83 25 12.6 7.02 24 14.4 6.16 27 16.45.41 92 16.7 5.30 100 17.0 5.22 45 17.4 5.08 18 18.1 4.90 25 18.8 4.7036 19.5 4.56 13 20.1 4.41 47 21.6 4.12 12 22.4 3.97 40 24.7 3.60 12 25.13.55 21 25.5 3.49 90 26.1 3.41 42 26.8 3.32 36 29.9 2.99 13 33.2 2.70 1239.6 2.27 11

TABLE 43 Peak angle data of 6-D2 (Experiment Reference 6- SampleReference D2) (Pattern #3) 2-θ (º) d Value Rel. Intensity (%) 8.4 10.4719 9.1 9.76 28 11.2 7.88 14 12.5 7.06 16 14.3 6.19 22 16.3 5.43 86 16.65.32 79 16.9 5.24 27 17.4 5.09 14 18.0 4.91 19 18.8 4.72 33 19.4 4.57 1120.1 4.42 49 22.3 3.98 49 22.5 3.95 30 22.9 3.89 14 23.1 3.85 10 24.83.59 15 25.1 3.55 23 25.5 3.49 100 26.1 3.41 44 26.8 3.33 34 27.2 3.2811 29.9 2.99 12

TABLE 44 Peak angle data of 6-E1 (Experiment Reference 6-SampleReference E1) (Pattern #4b) Rel. 2-θ (°) d Value Intensity (%) 9.3 9.5128 14.5 6.12 12 15.7 5.63 10 16.6 5.35 81 17.0 5.21 22 17.3 5.11 17 17.75.00 13 18.3 4.84 26 19.5 4.54 32 20.4 4.34 13 21.5 4.12 18 22.3 3.98 1422.6 3.94 21 23.4 3.80 11 23.9 3.72 13 25.8 3.45 100 26.4 3.38 16 27.13.29 24 27.5 3.25 20 30.2 2.95 14

TABLE 45 Peak angle data of 6-E2 (Experiment Reference 6-SampleReference E2) (Pattern #4b) Rel. 2-θ (°) d Value Intensity (%) 6.7 13.1411 8.3 10.69 37 9.1 9.76 30 11.2 7.87 17 14.2 6.23 12 15.6 5.67 17 16.35.43 78 16.7 5.29 20 17.2 5.14 21 18.1 4.90 22 18.8 4.71 11 19.3 4.60 2620.3 4.37 13 21.4 4.14 16 22.3 3.98 17 22.6 3.93 13 23.8 3.74 17 25.13.54 13 25.5 3.49 100 26.8 3.33 20 27.2 3.27 16

TABLE 46 Peak angle data of 6-F1 (Experiment Reference 6-SampleReference F1) (Pattern #5) Rel. 2-θ (°) d Value Intensity (%) 8.3 10.7047 9.1 9.71 37 11.1 7.98 46 14.3 6.21 12 15.4 5.75 39 16.3 5.42 64 16.95.23 58 17.4 5.09 10 18.0 4.91 18 19.1 4.64 16 20.0 4.44 40 21.4 4.15 5722.5 3.95 35 23.6 3.77 44 23.9 3.72 29 25.0 3.55 18 25.5 3.49 100 26.83.32 24 30.1 2.96 21

TABLE 47 Peak angle data of 6-F2 (Experiment Reference 6-SampleReference F2) (Pattern #4a) Rel. 2-θ (°) d Value) Intensity (%) 8.210.72 90 9.1 9.75 34 11.3 7.84 50 12.7 6.95 20 14.2 6.22 14 15.7 5.65 3115.7 5.66 27 16.3 5.43 88 17.2 5.16 46 18.1 4.91 23 18.9 4.70 12 19.24.62 17 20.4 4.35 34 21.6 4.12 40 22.4 3.97 13 22.7 3.92 25 23.9 3.73 3525. 3.54 15 25.6 3.48 100 26.8 3.32 24 27.2 3.27 12 29.9 2.98 11

TABLE 48 Peak angle data of 6-H1 (Experiment Reference 6-SampleReference H1) (Pattern #2d) Rel. 2-θ (°) d Value Intensity (%) 7.9 11.2415 9.1 9.68 31 14.3 6.20 16 16.3 5.43 91 17.6 5.03 21 18.1 4.89 20 18.94.70 11 20.0 4.44 32 21.2 4.18 22 22.2 4.00 45 25.3 3.52 34 25.6 3.48100 26.0 3.42 38 26.9 3.31 26 27.0 3.30 19

TABLE 49 Peak angle data of 6-H2 (Experiment Reference 6-SampleReference H2) (Pattern #2b) Rel. 2-θ (°) d Value Intensity (%) 9.0 9.8020 14.2 6.24 12 15.6 5.69 10 16.3 5.45 74 17.4 5.09 13 18.0 4.92 22 22.14.01 17 22.5 3.94 16 25.1 3.55 18 25.5 3.49 100 26.0 3.43 10 26.8 3.3324 27.2 3.28 13

TABLE 50 Peak angle data of 6-I1 (Experiment Reference 6-SampleReference I1) (Pattern #1) Rel. 2-θ (°) d Value Intensity (%) 6.8 12.9711 9.1 9.68 20 14.3 6.19 11 16.4 5.40 66 16.8 5.26 33 17.6 5.03 16 18.24.87 29 18.9 4.68 10 19.4 4.57 48 20.3 4.37 11 22.3 3.98 21 22.4 3.96 2623.2 3.83 14 25.6 3.47 100 26.3 3.39 17 26.9 3.31 22 27.3 3.26 24

TABLE 51 Peak angle data of 6-I2 (Experiment Reference 6-SampleReference I2) (Pattern #1) Rel. 2-θ (°) d Value Intensity (%) 6.7 13.1717 9.1 9.76 25 14.2 6.23 11 16.3 5.43 74 16.7 5.29 38 17.5 5.07 13 17.84.99 17 18.1 4.89 28 19.3 4.59 49 22.3 3.98 22 22.5 3.95 12 23.1 3.84 1425.2 3.53 15 25.5 3.49 100 26.2 3.40 13 26.8 3.32 21 27.2 3.27 23

TABLE 52 Peak angle data of 6-J1 (Experiment Reference 6-SampleReference J1) (Pattern #8) Rel. 2-θ (°) d Value Intensity (%) 7.6 11.5952 9.1 9.70 24 12.2 7.24 14 15.6 5.68 11 15.9 5.57 100 16.4 5.41 81 18.14.91 17 19.1 4.64 34 20.6 4.30 54 20.8 4.27 33 21.9 4.05 13 22.6 3.92 1224.3 3.66 72 25.0 3.56 16 25.6 3.48 73 26.9 3.32 17 27.3 3.27 13

TABLE 53 Peak angle data of 6-K1 (Experiment Reference 6-SampleReference K1) (Pattern #4a) Rel. 2-θ (°) d Value Intensity (%) 8.2 10.7460 9.1 9.74 37 11.3 7.85 68 12.8 6.90 17 14.2 6.22 14 15.6 5.69 40 16.35.43 88 17.0 5.20 57 17.4 5.09 11 18.0 4.91 19 19.1 4.65 20 20.2 4.38 4721.3 4.17 18 21.5 4.14 55 22.6 3.93 29 23.7 3.75 52 24.4 3.65 13 25.03.55 20 25.5 3.49 100 26.8 3.33 20 27.2 3.28 16 30.8 2.90 12

TABLE 54 Peak angle data of 6-L1 (Experiment Reference 6-SampleReference L1) (Pattern #13) Rel. 2-θ (°) d Value Intensity (%) 8.1 10.9128 18.1 4.89 18 18.9 4.69 10 19.7 4.50 42 20.9 4.24 19 21.9 4.05 27 22.73.91 16 23.4 3.81 12 24.5 3.64 12 25.0 3.56 59 25.6 3.47 100 9.1 9.68 2326.9 3.31 19 28.7 3.11 12 10.5 8.41 19 14.3 6.19 11 16.0 5.53 78 16.45.41 75 17.5 5.07 37

TABLE 55 Peak angle data of 6-L2 (Experiment Reference 6-SampleReference L2) (Pattern #2b) Rel. 2-θ (°) d Value Intensity (%) 9.1 9.7541 9.8 8.98 14 14.2 6.21 15 15.6 5.69 20 16.3 5.42 92 17.1 5.18 24 17.45.09 22 18.1 4.90 32 18.4 4.83 11 18.8 4.71 12 19.5 4.54 11 21.0 4.23 1122.4 3.97 20 22.6 3.94 19 24.7 3.60 40 25.6 3.48 100 26.8 3.32 25 27.23.27 10

TABLE 56 Peak angle data of 6-M1 (Experiment Reference 6-SampleReference M1) (Pattern #1) Rel. 2-θ (°) d Value Intensity (%) 8.1 10.9128 9.1 9.68 23 10.5 8.41 19 14.3 6.19 11 16.0 5.53 78 16.4 5.41 75 17.55.07 37 18.1 4.89 18 18.9 4.69 10 19.7 4.50 42 20.9 4.24 19 21.9 4.05 2722.7 3.91 16 23.4 3.81 12 24.5 3.64 12 25.0 3.56 59 25.6 3.47 100 26.93.31 19 28.7 3.11 12

TABLE 57 Peak angle data of 6-M2 (Experiment Reference 6-SampleReference M2) (Pattern #1) Rel. 2-θ (°) d Value Intensity (%) 6.7 13.1516 9.0 9.77 28 14.2 6.23 10 16.3 5.43 77 16.8 5.28 49 17.5 5.07 14 17.84.99 19 18.1 4.89 25 19.3 4.59 48 20.2 4.39 13 22.3 3.98 22 23.1 3.84 1224.6 3.61 20 25.2 3.53 14 25.5 3.48 100 26.2 3.40 14 26.8 3.32 20 27.33.27 20

TABLE 58 Peak angle data of 6-N2 (Experiment Reference 6-SampleReference N2) (Pattern #1) Rel. 2-θ (°) d Value Intensity (%) 9.0 9.7821 14.2 6.23 12 16.3 5.44 69 16.7 5.30 35 17.4 5.08 11 17.8 4.98 14 18.14.90 20 19.3 4.60 37 22.3 3.99 24 22.4 3.97 23 23.1 3.85 16 24.6 3.61 1225.5 3.49 100 26.2 3.40 13 26.8 3.33 23 27.2 3.28 19

TABLE 59 Peak angle data of 6-O1 (Experiment Reference 6- SampleReference O1) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.8 13.0622 8.1 10.88 12 9.1 9.70 43 11.2 7.90 10 13.0 6.83 10 14.3 6.20 17 16.45.41 100 16.8 5.28 48 17.5 5.06 15 17.9 4.95 16 18.2 4.88 31 18.9 4.7011 19.4 4.58 53 19.6 4.52 16 20.2 4.39 13 21.3 4.17 11 21.4 4.15 10 21.84.08 15 22.4 3.97 25 23.2 3.83 16 23.5 3.78 16 25.2 3.53 33 25.5 3.49 9426.2 3.40 12 26.8 3.32 29 27.1 3.29 23 30.1 2.97 13

TABLE 60 Peak angle data of 6-P2 (Experiment Reference 6- SampleReference P2) (Pattern #4a) 2-θ (º) d Value Rel. Intensity (%) 8.2 10.7471 9.0 9.78 38 11.2 7.88 23 12.7 6.96 14 14.2 6.23 16 15.6 5.69 17 16.35.43 90 17.1 5.18 28 17.3 5.13 17 18.0 4.91 18 19.2 4.63 10 20.3 4.37 1321.5 4.14 28 22.4 3.97 13 22.6 3.93 16 23.8 3.73 24 25.1 3.54 14 25.53.49 100 26.8 3.33 22

TABLE 61 Peak angle data of 6-Q2 (Experiment Reference 6- SampleReference Q2) (Pattern #2b) 2-θ (º) d Value Rel. Intensity (%) 9.1 9.7340 14.3 6.21 16 15.5 5.70 22 16.3 5.42 87 17.0 5.22 18 17.4 5.08 18 18.14.89 31 18.8 4.71 12 19.5 4.54 11 20.9 4.24 12 21.5 4.12 4 22.4 3.97 1722.6 3.93 21 24.8 3.59 26 25.6 3.48 100 26.8 3.32 25 27.2 3.28 11

TABLE 62 Peak angle data of 6-R1 (Experiment Reference 6- SampleReference R1) (Pattern #3) 2-θ (º) d Value Rel. Intensity (%) 8.4 10.4612 9.1 9.74 23 14.4 6.16 13 14.4 6.13 12 16.4 5.42 71 16.6 5.34 52 16.85.26 30 18.1 4.91 26 18.7 4.73 29 20.1 4.42 34 22.3 3.99 44 22.4 3.97 3824.7 3.60 16 25.1 3.55 21 25.5 3.49 100 26.0 3.43 38 26.7 3.34 31 27.23.27 14 29.8 2.99 10

TABLE 63 Peak angle data of 6-S1 (Experiment Reference 6- SampleReference S1) (Pattern #6a) 2-θ (º) d Value Rel. Intensity (%) 12.9 6.8421 16.5 5.36 51 19.3 4.59 30 19.5 4.55 100 20.6 4.31 49 22.0 4.03 3125.3 3.52 44 26.0 3.42 64 28.1 3.18 10 33.4 2.68 15

TABLE 64 Peak angle data of 7-A2 (Experiment Reference 7- SampleReference A2) (Pattern #19) 2-θ (º) d Value Rel. Intensity (%) 9.1 9.7218 16.5 5.37 26 16.9 5.25 18 17.9 4.96 13 19.3 4.60 25 20.5 4.33 43 22.73.91 77 25.3 3.51 100 26.6 3.35 21 27.1 3.29 43 29.7 3.01 13

TABLE 65 Peak angle data of 7-B1 (Experiment Reference 7- SampleReference B1) (Pattern #2a) 2-θ (º) d Value Rel. Intensity (%) 9.2 9.6241 12.4 7.15 30 14.3 6.17 17 15.8 5.60 33 16.4 5.39 85 17.2 5.16 73 18.24.87 29 20.8 4.26 25 21.0 4.23 28 21.6 4.10 14 22.4 3.97 16 22.9 3.88 3023.0 3.86 36 25.0 3.56 23 25.7 3.46 100 26.9 3.31 26 27.4 3.26 36 28.73.10 12

TABLE 66 Peak angle data of 7-C1 (Experiment Reference 7- SampleReference C1) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.8 12.9110 9.2 9.63 24 14.3 6.19 11 16.5 5.38 70 16.7 5.29 34 17.7 5.00 14 18.24.87 28 19.4 4.56 36 22.5 3.96 22 22.4 3.96 22 23.2 3.83 12 25.6 3.47100 26.3 3.39 14 27.0 3.30 27 27.2 3.27 25

TABLE 67 Peak angle data of 7-C2 (Experiment Reference 7- SampleReference C2) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 9.1 9.7523 14.2 6.22 11 16.3 5.42 72 16.7 5.30 31 17.5 5.07 14 17.7 5.01 12 18.14.89 26 19.3 4.59 37 22.3 3.98 22 23.1 3.84 14 23.7 3.75 6 25.1 3.54 1625.6 3.48 100 26.2 3.40 13 26.8 3.32 21 27.3 3.27 24

TABLE 68 Peak angle data of 7-D1 (Experiment Reference 7- SampleReference D1) (Pattern #3) 2-θ (º) d Value Rel. Intensity (%) 8.5 10.3925 9.1 9.67 26 11.3 7.81 20 12.6 7.00 19 14.4 6.14 32 16.5 5.38 71 16.75.29 100 16.9 5.23 57 17.5 5.07 13 18.1 4.88 19 18.9 4.69 36 19.5 4.5410 20.2 4.39 46 21.7 4.10 14 22.4 3.96 49 22.6 3.93 30 24.8 3.59 24 25.63.47 74 26.2 3.40 40 26.9 3.31 34

TABLE 69 Peak angle data of 7-D2 (Experiment Reference 7- SampleReference D2) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.7 13.1811 9.0 9.78 17 14.2 6.23 11 16.3 5.44 67 16.7 5.30 43 17.4 5.09 15 17.75.00 18 18.1 4.90 30 19.3 4.60 57 20.2 4.40 14 21.2 4.18 12 22.3 3.99 3022.5 3.95 11 23.1 3.85 14 24.6 3.62 11 25.5 3.49 100 26.1 3.41 21 26.83.32 20 27.2 3.27 27

TABLE 70 Peak angle data of 7-E2 (Experiment Reference 7- SampleReference E2) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.7 13.1411 9.0 9.77 24 10.9 8.14 11 12.2 7.26 15 12.8 6.90 12 14.2 6.24 10 15.55.73 14 16.1 5.50 43 16.3 5.44 68 16.7 5.30 37 17.4 5.08 19 17.7 5.01 2318.1 4.90 26 19.3 4.60 52 20.2 4.40 14 21.2 4.19 42 22.0 4.04 10 22.33.99 23 23.1 3.85 16 25.4 3.51 79 25.5 3.49 100 26.1 3.41 12 26.8 3.3317 27.2 3.27 23 30.0 2.98 10

TABLE 71 Peak angle data of 7-F1 (Experiment Reference 7- SampleReference F1) (Pattern #5) 2-θ (º) d Value Rel. Intensity (%) 8.2 10.7458 9.1 9.74 10 11.1 7.99 57 12.8 6.92 12 15.4 5.75 65 16.2 5.45 24 17.05.22 100 17.9 4.95 10 19.1 4.64 22 20.0 4.43 55 21.4 4.15 84 22.2 4.0125 22.5 3.95 31 23.6 3.77 58 24.0 3.70 28 25.5 3.50 50 30.3 2.95 24

TABLE 72 Peak angle data of 7-G1 (Experiment Reference 7- SampleReference G1) (Pattern #9) 2-θ (º) d Value Rel. Intensity (%) 7.9 11.2120 9.1 9.76 15 14.2 6.24 10 15.7 5.62 70 16.3 5.44 47 16.9 5.24 32 18.04.92 12 19.3 4.60 40 20.6 4.31 22 21.6 4.10 29 22.2 4.00 12 24.5 3.64 8825.1 3.54 46 25.4 3.50 100 26.1 3.41 13 26.7 3.33 22 28.6 3.12 22 29.92.99 11

TABLE 73 Peak angle data of 7-G2 (Experiment Reference 7- SampleReference G2) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 9.0 9.8020 16.3 5.44 64 16.7 5.30 34 17.4 5.09 12 17.7 5.00 15 18.1 4.90 19 19.34.60 49 20.2 4.40 10 21.2 4.18 11 22.3 3.99 25 23.0 3.86 13 25.1 3.54 1325.5 3.49 100 26.1 3.41 14 26.8 3.33 17 27.2 3.27 20

TABLE 74 Peak angle data of 7-H2 (Experiment Reference 7- SampleReference H2) (Pattern #2b) Rel. d Intensity 2-θ (º) Value (%) 9.0 9.8018 14.2 6.24 10 16.1 5.49 25 17.4 5.09 11 18.0 4.92 17 21.2 4.19 15 22.63.93 11 23.1 3.85 11 25.2 3.53 18 25.5 3.49 100 26.8 3.33 21

TABLE 75 Peak angle data of 7-I1 (Experiment Reference 7- SampleReference I1) (Pattern #1) Rel. d Intensity 2-θ (º) Value (%) 9.1 9.6923 16.4 5.41 70 16.8 5.28 29 17.5 5.06 11 18.2 4.88 25 19.4 4.58 32 22.43.97 26 23.2 3.84 11 25.3 3.52 14 25.6 3.48 100 26.2 3.39 11 26.9 3.3121 27.3 3.26 21 30.0 2.97 11

TABLE 76 Peak angle data of 7-I2 (Experiment Reference 7- SampleReference I2) (Pattern #1) Rel. d Intensity 2-θ (º) Value (%) 6.8 13.0712 9.1 9.72 27 14.3 6.20 13 16.4 5.41 78 16.8 5.29 43 17.5 5.06 13 17.84.98 17 18.2 4.88 28 18.9 4.70 11 19.4 4.58 48 20.3 4.38 11 21.3 4.17 1322.1 4.01 10 22.4 3.97 23 23.2 3.84 16 25.2 3.53 15 25.6 3.48 100 26.23.40 15 26.9 3.31 21 27.3 3.26 23

TABLE 77 Peak angle data of 7-J1 (Experiment Reference 7- SampleReference J1) (Pattern #2a) Rel. d Intensity 2-θ (º) Value (%) 9.0 9.7916 16.3 5.45 65 16.9 5.23 19 18.0 4.93 18 25.0 3.56 16 25.5 3.49 10026.7 3.33 26 27.1 3.28 19 29.9 2.99 12

TABLE 78 Peak angle data of 7-J2 (Experiment Reference 7- SampleReference J2) (Pattern #2a) Rel. d Intensity 2-θ (º) Value (%) 9.0 9.7920 12.2 7.24 10 14.2 6.24 12 15.6 5.67 12 16.3 5.44 70 17.0 5.22 29 18.04.92 20 20.6 4.30 15 22.2 3.99 11 22.9 3.89 20 25.1 3.55 17 25.5 3.49100 26.7 3.33 25 27.2 3.28 22 29.9 2.99 12

TABLE 79 Peak angle data of 7-L2 (Experiment Reference 7- SampleReference L2) (Pattern #2a) Rel. d Intensity 2-θ (º) Value (%) 9.0 9.8024 14.2 6.24 10 16.0 5.52 11 16.3 5.44 59 16.7 5.30 24 17.4 5.10 11 17.75.00 11 18.1 4.91 23 19.3 4.60 36 22.3 3.99 19 23.1 3.85 12 25.1 3.54 1025.5 3.49 100 26.1 3.41 11 26.8 3.33 23 27.2 3.27 20

TABLE 80 Peak angle data of 7-M1 (Experiment Reference 7- SampleReference M1) (Pattern #2a) Rel. d Intensity 2-θ (º) Value (%) 9.1 9.7325 14.2 6.22 13 15.6 5.67 11 16.3 5.42 75 17.0 5.21 20 18.1 4.90 20 18.84.71 11 22.3 3.98 12 25.6 3.48 100 26.8 3.32 26 27.2 3.27 21 29.9 2.9810

TABLE 81 Peak angle data of 7-M2 (Experiment Reference 7- SampleReference M2) (Pattern #2a) Rel. d Intensity 2-θ (º) Value (%) 9.1 9.7627 12.2 7.22 24 14.2 6.22 14 15.6 5.67 36 15.9 5.56 18 16.3 5.43 78 17.05.21 64 17.4 5.09 11 18.1 4.90 26 18.8 4.71 11 19.3 4.59 15 20.6 4.30 2821.0 4.23 22 21.5 4.13 16 22.3 3.98 14 22.9 3.89 39 24.8 3.59 34 25.53.48 100 26.8 3.32 26 27.3 3.27 45 28.6 3.11 11 29.9 2.98 11

TABLE 82 Peak ang0le data of 7-N1 (Experiment Reference 7- SampleReference N1) (Pattern #7) Rel. d Intensity 2-θ (º) Value (%) 7.2 12.2717 9.1 9.72 27 14.2 6.22 12 15.9 5.58 62 16.3 5.43 86 16.7 5.32 19 17.55.06 11 18.1 4.89 25 19.3 4.59 26 19.7 4.50 25 20.8 4.27 14 21.2 4.18 2222.4 3.97 18 24.8 3.58 83 25.5 3.48 100 26.8 3.32 23 27.2 3.28 19 30.02.98 10

TABLE 83 Peak angle data of 7-O2 (Experiment Reference 7- SampleReference O2) (Pattern #2a) Rel. d Intensity 2-θ (º) Value (%) 9.0 9.7923 12.2 7.24 20 14.2 6.24 13 15.6 5.67 26 15.9 5.56 14 16.3 5.43 78 17.05.21 49 17.4 5.10 13 18.0 4.92 21 20.6 4.30 22 21.0 4.23 15 22.9 3.89 3025.0 3.56 15 25.5 3.49 100 26.8 3.33 22 27.3 3.27 28

TABLE 84 Peak angle data of 7-P1 (Experiment Reference 7- SampleReference P1) (Pattern #10) Rel. d Intensity 2-θ (º) Value (%) 8.2 10.7732 10.9 8.14 30 15.2 5.82 32 16.2 5.47 20 16.8 5.26 100 17.8 4.98 1219.1 4.65 17 19.8 4.49 47 21.3 4.17 68 21.8 4.08 32 22.1 4.01 29 22.53.95 10 23.4 3.79 66 23.6 3.76 41 25.3 3.51 62 26.1 3.41 14 26.7 3.34 2129.7 3.00 27 34.7 2.58 11

TABLE 85 Peak angle data of 7-Q1 (Experiment Reference 7- SampleReference Q1) (Pattern #11) Rel. d Intensity 2-θ (º) Value (%) 7.4 11.8853 10.6 8.32 13 11.1 7.96 12 16.1 5.52 91 17.2 5.14 17 18.0 4.92 12 20.24.39 100 20.7 4.28 15 21.5 4.13 48 22.6 3.93 18 23.8 3.73 13 23.9 3.7213 25.1 3.54 19 25.5 3.49 32 25.7 3.46 20 26.7 3.34 12

TABLE 86 Peak angle data of 7-R1 (Experiment Reference 7- SampleReference R1) (Pattern #1) Rel. d Intensity 2-θ (º) Value (%) 16.2 5.4548 18.0 4.92 17 18.7 4.75 15 19.2 4.62 29 20.0 4.43 16 22.1 4.01 26 22.33.98 22 22.9 3.87 12 25.4 3.50 100 25.9 3.44 23 26.7 3.34 26 27.1 3.2829 29.9 2.99 13

TABLE 87 Peak angle data of 7-S1 (Experiment Reference 7- SampleReference S1) (Pattern #8, amorphized) Rel. d Intensity 2-θ (º) Value(%) 13.0 6.83 28 16.6 5.33 20 19.3 4.59 44 19.5 4.56 80 25.2 3.54 6725.9 3.43 100 26.1 3.41 67 28.3 3.15 52 33.7 2.66 25 37.7 2.38 20

c. Conclusion

Powder diffraction patterns of wetted pellets tended to exhibit greaterincoherence and higher background. During drying the solvent wetspecimens resembling Pattern #1 frequently underwent form change.Patterns #3 and #6a were identified as single melt event forms (bothmelt events approximately coincided) and Pattern #6b was determined ashigher melt forms from water (Patterns #6a and #6b were approximatelyisostructural by XRPD).

Pattern #3 contained toluene (th., 0.25% w/w toluene solvate), releasedas a discrete transition before melting (FIG. 330 ). TG analysis ofPattern #3 specimen exhibited a weight loss transition consistent withtoluene release (th., 0.25% w/w toluene solvate), prior to melting andmay result in re-organization when released (FIG. 329 ).

Pattern #6a, was anhydrous and TGA −Δ wt. Transition was absent pre-meltand ablative post melt, which is consistent with decomposition (FIG. 347).

Pattern #6b specimen may contain crystal bonded acetonitrile andmethanol and cannot be oven dried (FIG. 353 ) TG analyses performed onthe specimen corresponding to Pattern #6b exhibited a weight losstransition in the vicinity of melting and was attributed to crystalbonded acetonitrile and methanol (FIG. 352 );

Patterns #3, #6a, and #6b require further investigation as they mayprovide access to polymorphic forms with desirable physical properties:

-   -   Pattern #6a specimen was placed in vacuum oven for an additional        72 h at 40° C. and the solvent content was quantified by ¹H NMR        spectroscopy after this treatment (methanol 0.6% w/w,        acetonitrile n.d.), supporting our belief that methanol is        strongly bonded;    -   potentially, maturation of Patterns #3 and #6b specimens, in an        aqueous solvent, such as ethanol at moderate water activity may        be applied to break the solvates;    -   judging the two powder patterns, Pattern #6a/b is preferred over        Pattern #3 and #6 appears to belong to a more symmetrical,        crystallographic space group;    -   Pattern #6a (m.p.>189° C.) is now the desired form.

vii. Form Control: Suspension Equilibration in Water at 20° C.(Experiment Reference 8)

a. Experimental Procedure

The tabernanthalog monofumarate salt (Sample Reference 1, Pattern #1,1.0 g, 1 wt) was suspended in water (5 ml, 5 vol) at 20° C. for 10 days(the suspension was sub-sampled to monitor the conversion to Pattern #6aby XRPD). The suspension was filtered through a sintered funnel and thefilter cake was dried under nitrogen flow for ca. 24 h. Sample 8-A4(Experiment Reference 8-Sample Reference A4) was collected as a brownsolid (560.6 mg, 56% yield uncorr.). Yield was not corrected forimpurities, solvents, etc.

b. Analytical Characterization Data

¹H NMR

¹H NMR spectrum of 8-A4 (Experiment Reference 8-Sample Reference A4) wasacquired in DMSO-d₆ and calibrated to the non-deuterated solventresidual at 2.50 ppm API to Fumaric acid, 1.0 to 1.0 is provided in FIG.146 . ¹H NMR spectra overlay of 8-A4 (Experiment Reference 8-SampleReference A4) and input (Sample Reference 1) is presented in FIG. 147 .

TGA

TGA profile of 8-A4 (Experiment Reference 8-Sample Reference A4),analysis was acquired at a ramp rate of +10° C./minute, is presented inFIG. 148 .

DSC

DSC profile of 8-A4 (Experiment Reference 8-Sample Reference A4),analysis was acquired at a ramp rate of +10° C./minute, is provided inFIG. 149 .

XRPD

The XRPD profile of 8-A4 (Experiment Reference 8-Sample Reference A4)(Form A) is presented in FIG. 150 and the peaks are provided in Table88.

TABLE 88 Peak angle data of 8-A4 (Experiment Reference 8- SampleReference A4) (Form A, Pattern #6a) Rel. d Intensity 2-θ (º) Value (%)12.9 6.85 12 16.5 5.37 74 19.2 4.61 27 19.5 4.56 100 20.6 4.32 90 22.04.04 32 25.2 3.52 81 26.0 3.43 56 28.0 3.18 12 33.4 2.68 17

HPLC

The HPLC profile of 8-A4 (Experiment Reference 8-Sample Reference A4) ispresented in FIG. 151 .

PLM

PLM results are shown in FIGS. 152-155 .

c. Conclusion

The suspension was sub-sampled, and the wet pellet was analyzed by XRPDuntil complete conversion was achieved (FIG. 156 ). The tabernanthalogmonofumarate salt (Sample Reference 1, Pattern #1) was successfullyconverted to the desired form (Pattern #6a, Form A, FIG. 157 ).Optically, the crystallographic quality of the batch was not judgedsuitable for SC-XRD.

viii. Thermocycling (Experiment Reference 9)

a. Experimental Procedure

The tabernanthalog monofumarate salt (Pattern #1, 75 mg, 1 wt) wasweighed out in to 4 separate vials and the corresponding solvents (750μl, 10 vol) from Table 89 were charged.

The suspensions underwent constant amplitude thermocycling at +0.5°C./min up to 75% of the relevant solvent b.p. and −0.5° C./min down to20° C. The thermocycle was repeated 5 times for 9-A (ExperimentReference 9-Sample Reference A) to 9-D (Experiment Reference 9-SampleReference D) prior to working up the samples, analyzed the by XRPD (wetand dry). 9-E (Experiment Reference 9-Sample Reference E) and 9-F(Experiment Reference 9-Sample Reference F) were subjected to 10 cyclesand 9-G (Experiment Reference 9-Sample Reference G) to 35 cycles.

TABLE 89 Thermocycle experiment setup description Input Number Ref-Input weights b.p. Thermocycle of erences reference (mg) Solvent (° C.)peak T (° C.) cycles) 9-A Sample 75.5 Water 100 75  5 9-B Reference 175.7 TBME  55 41  5 9-C 75.1 iPAC  89 69  5 9-D 75.5 Toluene 110 83  59-E 75.3 Water 100 75 10 9-F 8-A4 75.2 Water 100 75 10 (ExperimentReference 8- Sample Reference A4) 9-G Sample 75.4 Water 100 75 35Reference 1

b. Analytical Characterization Data

Thermocycling in different solvents can promote the formation ofalternative polymorphic forms. The tabernanthalog monofumarate salt(Pattern #1), was heated and cooled between 20° C. and 75% of therelevant solvent b.p. at 0.5° C./minute, for 5 consecutive cycles; a10-minute dwell was incorporated at each inflection. Thermocycling isripening technique, that encourages particle size enlargement andpromotes the evolution of the API into a stable phase. Smaller, lessstable particles dissolve as the upper temperature boundary isapproached, leaving larger stable particles behind; during cooling theconcentrated supernatant de-supersaturates resulting in growth in thepresence of the larger particles; after thermocycling, the particlesshould be larger and fewer in number. The products were analyzed bothwet and dry to determine if form changes had occurred, all products wereconsistent with previously encountered patterns, and by DSC none of theproducts were single phase.

For samples that contain wet pellets, suffix 1 is used. For oven-driedsamples, suffix 2 is used.

¹H NMR

The relevant NMR spectra are provided in FIGS. 158-163 .

TGA

The relevant TGA profiles are provided in FIGS. 164-169 .

DSC

The relevant DSC profiles are provided in FIGS. 170-176 .

XRPD

The relevant XRD data is provided in FIGS. 177-190 and Tables 90−103.

TABLE 90 Peak angle data of 9-A1 (Experiment Reference 9-SampleReference A1) 2-θ (º) d Value Rel. Intensity (%) 9.1 9.71 100 16.3 5.4520 25.1 5 3.55 23 25.5 3.49 18

TABLE 91 Peak angle data of 9-A2 (Experiment Reference 9-SampleReference A2) (Pattern #2c) 2-θ (º) d Value Rel. Intensity (%) 9.1 9.7462 14.2 6.21 23 16.3 5.42 91 17.5 5.08 14 18.1 4.90 21 19.5 4.55 29 22.04.03 13 22.2 4.00 13 25.1 3.54 29 25.6 3.48 100 26.1 3.42 19 26.8 3.3220

TABLE 92 Peak angle data of 9-B1 (Experiment Reference 9-SampleReference B1) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 6.8 13.0412 9.1 9.69 23 14.3 6.21 11 16.4 5.41 69 16.8 5.28 39 17.6 5.04 17 17.84.98 19 18.2 4.88 29 19.4 4.58 50 20.2 4.38 12 22.1 4.01 11 22.4 3.97 2523.2 3.83 13 25.3 3.52 18 25.6 3.48 100 26.2 3.39 16 26.9 3.31 21 27.33.27 28

TABLE 93 Peak angle data of 9-B2 (Experiment Reference 9-SampleReference B2) (Pattern #1) 2-θ (º) d Value Rel. Intensity (%) 9.0 9.7815 14.2 6.23 10 16.3 5.43 58 16.7 5.29 38 17.4 5.08 11 17.8 4.98 12 18.14.90 24 19.3 4.60 51 20.2 4.40 13 22.3 3.98 24 23.1 3.85 15 25.5 3.49100 26.2 3.40 15 26.8 3.32 20 27.2 3.28 27

TABLE 94 Peak angle data of 9-C1 (Experiment Reference 9-SampleReference C1) (Pattern #8) Rel. Intensity 2-θ (°) d Value (%) 7.6 11.6640 9.1 9.76 21 12.2 7.27 13 15.5 5.69 10 15.8 5.59 100 16.3 5.43 71 18.04.92 17 19.1 4.65 45 20.6 4.31 56 21.9 4.06 20 23.8 3.73 19 24.2 3.67 9024.9 3.57 19 25.5 3.49 78 26.8 3.33 18 27.2 3.27 17

TABLE 95 Peak angle data of 9-C2 (Experiment Reference 9-SampleReference C2) (Pattern #8) Rel. Intensity 2-θ (°) d Value (%) 7.6 11.6739 9.0 9.78 21 12.2 7.27 12 14.2 6.23 11 15.9 5.58 100 16.3 5.42 78 17.45.08 11 18.0 4.92 16 18.9 4.69 11 19.1 4.65 37 20.6 4.31 52 21.9 4.05 1523.8 3.73 14 24.3 3.66 84 25.0 3.56 14 25.6 3.48 81 26.3 3.38 6 26.83.33 16 27.3 3.27 15

TABLE 96 Peak angle data of 9-D1 (Experiment Reference 9-SampleReference D1) (Pattern #3) Rel. Intensity 2-θ (°) d Value (%) 8.4 10.5424 9.0 9.80 29 9.7 9.08 10 11.1 7.95 28 12.4 7.12 23 14.4 6.16 23 16.35.43 83 16.6 5.35 94 16.8 5.26 42 17.3 5.11 10 18.0 4.92 19 18.7 4.73 4220.1 4.42 59 21.6 4.11 10 22.2 4.00 47 22.5 3.94 25 22.8 3.90 13 24.63.61 20 25.0 3.56 25 25.5 3.49 100 26.0 3.42 62 26.7 3.33 31

TABLE 97 Peak angle data of 9-D2 (Experiment Reference 9-SampleReference D2) (Pattern #3) Rel. Intensity 2-θ (°) d Value (%) 8.4 10.5014 9.0 9.78 18 11.1 7.93 24 12.4 7.10 16 14.4 6.15 18 16.3 5.43 75 16.65.34 76 16.9 5.26 32 17.4 5.10 10 18.0 4.91 18 18.8 4.73 33 20.1 4.41 5221.6 4.11 11 22.2 4.00 43 22.5 3.95 23 22.8 3.90 11 24.7 3.61 21 25.03.56 20 25.5 3.49 100 26.0 3.42 53 26.7 3.33 32 29.9 2.98 11

TABLE 98 Peak angle data of 9-E1 (Experiment Reference 9-SampleReference E1) (Pattern #2c) Rel. Intensity 2-θ (°) d Value (%) 9.1 9.73100 14.2 6.23 20 16.3 5.44 69 17.4 5.09 15 18.0 4.92 12 19.4 4.56 3220.6 4.31 35 21.9 4.05 18 22.2 4.01 17 25.1 3.55 50 25.5 3.49 66 26.03.42 32 26.8 3.33 13 38.5 2.34 10

TABLE 99 Peak angle data of 9-E2 (Experiment Reference 9-SampleReference E2) (Pattern #2c) Rel. Intensity 2-θ (°) d Value (%) 9.1 9.7379 12.9 6.84 23 14.2 6.22 21 16.3 5.42 69 16.4 5.42 64 17.5 5.08 13 18.14.90 15 19.5 4.55 100 20.6 4.30 17 22.0 4.03 24 22.2 4.00 17 25.2 3.5435 25.6 3.48 68 26.1 3.42 65 26.8 3.32 17 27.2 3.27 10

TABLE 100 Peak angle data of 9-F1 (Experiment Reference 9-SampleReference F1) (Pattern #2c) Rel. Intensity 2-θ (°) d Value (%) 9.1 9.7393 12.9 6.85 49 14.2 6.23 16 16.3 5.42 60 17.4 5.09 10 18.0 4.92 13 19.44.57 100 20.6 4.30 33 21.9 4.05 19 22.2 4.00 10 25.1 3.55 22 25.5 3.4975 26.0 3.42 81 26.7 3.33 15 29.3 3.05 12

TABLE 101 Peak angle data of 9-F2 (Experiment Reference 9-SampleReference F2) (Pattern #2c) Rel. Intensity 2-θ (°) d Value (%) 9.1 9.7417 12.9 6.85 19 16.3 5.42 38 17.4 5.09 14 19.4 4.56 100 25.6 3.48 4026.0 3.42 86 26.8 3.32 10 31.2 2.87 13

TABLE 102 Peak angle data of 9-G1 (Experiment Reference 9-SampleReference G1) (Pattern #2c) Rel. Intensity 2-θ (°) d Value (%) 9.1 9.73100 14.2 6.24 18 16.3 5.45 54 18.0 4.92 11 19.5 4.56 13 21.9 4.06 1322.2 4.01 15 25.0 3.55 38 25.5 3.49 66 26.1 3.42 13 26.7 3.33 14 38.52.34 12

TABLE 103 Peak angle data of 9-G2 (Experiment Reference 9-SampleReference G2) (Pattern #2c) Rel. Intensity 2-θ (°) d Value (%) 9.2 9.5976 14.4 6.16 21 16.5 5.37 100 17.6 5.03 13 18.3 4.85 28 19.0 4.67 1219.7 4.51 11 22.4 3.97 16 22.3 3.98 16 22.5 3.94 17 25.4 3.50 45 25.73.46 100 27.0 3.30 27 27.4 3.26 12

PLM

PLM data is provided in FIGS. 191-198 .

c. Conclusion

9-A2 (Experiment Reference 9-Sample Reference A2) was a mixed phase byDSC; however, the highest melt event observed was ca 10° C. higher thanthe melt of Pattern #6a (onset 199° C., peak 203° C.). Therefore, twofollow-up experiments were performed which involved subjecting SampleReference 1 and 8-A (Experiment Reference 8-Sample Reference A; singlemelt form) to prolonged thermocycling in purified water (9-E (ExperimentReference 9-Sample Reference E) and 9-F (Experiment Reference 9-SampleReference F), respectively). The collected data are summarized in Table104.

TABLE 104 Summary for thermocycling experiment XRPD crystal Thermo-crystal- form ¹H NMR Input cycle linity change XRPD XRPD (solvent Ref-Input weights b.p. peak T (oven following Yield (moist (dried TGA (driedcontent, erences reference (mg) Solvent (° C.) (° C.) dried) dry %pellet) pellet) pellet) %w/w) 9-A Sample 75.5 Water 100 75 82.1% ✓ 31.0%Incoherent Pattern Flat — Reference 1 #2c baseline 9-B 75.7 TBME  55 4173.6% x 75.4% Pattern #1 Pattern −2.8% w/w  0.3% #1 (102.9° C.) 9-C 75.1iPAC  89 69 72.8% x 84.8% Pattern #8 Pattern −21.0% w/w 13.2% #8 (114.1°C.) 9-D 75.5 Toluene 110 83 74.5% x 56.2% Pattern #3 Pattern −9.1% w/w 6.0% #3 (126.0° C.) 9-E 75.3 Water 100 75 77.1% x 42.1% Pattern #2cPattern −3.4% w/w N/A #2c (155.1° C.) 9-F 8-A4 75.2 Water 100 75 82.3% ✓25.5% Pattern #2c Pattern −2.0% w/w N/A (Experiment #2c (146.3° C.)Reference 8- Sample Reference A4) 9-G Sample 75.4 Water 100 75 81.1% x21.5% Pattern #2c Pattern N/A N/A Reference 1 #2c

Comparative XRPD data is provided in FIGS. 199-206 .

9-E (Experiment Reference 9-Sample Reference E) and 9-F (ExperimentReference 9-Sample Reference F) formed consistent crystal structuresthroughout oven drying (FIG. 203 and FIG. 204 ). The same crystalstructure was formed for 9-A (Experiment Reference 9-Sample ReferenceA), (9-E (Experiment Reference 9-Sample Reference E) and 9-F (ExperimentReference 9-Sample Reference F) (FIG. 205 ). However, form change wasobserved in 9-F (Experiment Reference 9-Sample Reference F), whencompared to the input material of 8-A2 (Experiment Reference 8-SampleReference A2) which suggested that the crystal form evolved from thethermocycle could be more stable than the previous form following waterequilibration (FIG. 206 ). Therefore, 9-G (Experiment Reference 9-SampleReference G) was performed in purified water, applying 35 cycles toenforce the conversion to a single higher melt event material. The DSCprofile of the product obtained showed the same 3 melting point events(FIG. 176 ). The product from the thermocycle then underwentequilibration in purified water at 90° C. to attempt to evolve the phasesolely into the higher melt form, however, were not able to isolate thehigher melt event material (insufficient quantity for analysis, materialappeared as a film around the vial). Based on the above observations, anew form investigation was performed by preparing the hemi-fumarate saltin purified water in order to rule out the presence of tabernanthaloghemifumarate, or related metastable polymorphs (refer tore-proportionation investigation).

ix. Re-Proportionation Investigation (Experiment Reference 10)

a. Experimental Procedure

10-A: Tabernanthalog (native) (50.8 mg, 1 wt) and fumaric acid (6.8 mg,0.5 equiv) were charged into a vial. Purified water (250 ml, 5 vol) wassubsequently added, and the suspension was stirred at 50° C. for ca. 24h. The brown suspension was filtered through a sintered funnel and wasdried under nitrogen flow.

10-B: Tabernanthalog (native) (50.6 mg, 1 wt) and fumaric acid (8.9 mg,0.5 equiv) were charged into a vial. Purified water (250 ml, 5 vol) wassubsequently added, and the suspension was stirred at 20° C. for ca. 24h. The brown suspension was filtered through a sintered funnel and wasdried under nitrogen flow.

b. Analytical Characterization Data

DSC

DSC profiles are provided in FIGS. 207 and 208 .

XRPD

XRPD data is provided in FIG. 209 and Table 105.

TABLE 105 Peak angle data of 10-A1 (Experiment Reference 10-SampleReference A1) (Pattern #22) Rel. Intensity 2-θ (°) d Value (%) 10.5 8.4425 15.1 5.86 18 18.9 4.68 100 27.4 3.26 24

c. Conclusion

DSC analysis of this specimen (FIG. 210 , black thermogram 10-B1(Experiment Reference 10-Sample Reference B1)) exhibited 3 endothermicevents, one of which coincided with the new peak that was observedduring the thermocycling study (Experiment Reference 9). This phase thenunderwent crystallization into the stable hemi-fumarate at ca. 208° C.

Based on these results, the new higher melting form observed is mostlikely a disproportionated by-product (Tabernanthalog hemifumarate) andnot a supraordinate version of the tabernanthalog fumarate salt.Therefore, Form A is still the progressable stable form (8-A4)(Experiment Reference 8-Sample Reference A4).

x. Heat-Up/Cool Down (HUCD) Crystallization in Different Solvents(Experiment Reference 11)

a. Experimental Procedure

Separate portions of the tabernanthalog monofumarate salt (Pattern #1,Sample Reference 1, ca 75 mg, 1.0 wt.) were charged to separate vessels.The appropriate solvents (750 μl, 10.0 vol, refer to Table 106) werecharged to the relevant vessels and subsequent charges of theappropriate co-solvent were made to accomplish dissolution at reflux.The solutions were cooled to 18 to 23° C. and allowed to standundisturbed, until crystallization was judged complete. After this timethe products were isolated by centrifugation, washed with recycledmaturation solvent, dried under reduced pressure at 40° C. and analyzedby XRPD for evidence of alternative crystalline forms.

TABLE 106 HUCD screen setup description Experiment Co- Reference- Inputsolvents Key chemical Sample Input weights (volumes functional b.p. ICHReference reference (mg) Solvent A Solvent B added, μl) groups (° C.)Classes 11-A Tabernanthalog 74.7 Acetone water 80 Symmetrical 56 3fumarate ketone 11-B Sample 76.9 Acetonitrile water 120 Simple dipolar-82 2 Reference aprotic nitrile 11-C 1 77.6 Butanol water 60 Linearaliphatic 118 3 alcohol 11-D 76.7 tert-Butylmethyl methanol 2800Branched aliphatic 55 3 ether methoxy ether 11-E 75.7 Dichloromethanemethanol 880 Chlorinated 40 2 hydrocarbon 11-F 77.2 Ethanol water 60Linear aliphatic 78 3 alcohol 11-G 76.0 methyl acetate water/ 80Aliphatic ester 57 3 methanol 11-H 76.3 2-Propanol water 80 Branchedaliphatic 83 3 alcohol 11-1 77.4 methanol None N/A Linear aliphatic 65 3alcohol 11-J 76.2 Methylethyl water 60 Asymmetric dialkyl 80 3 ketoneketone 11-K 75.5 2-Methyl THF methanol 1560 Asymmetric cyclic 80 3 ether11-L 74.8 Tetrahydrofuran water 60 Symmetric cyclic 80 # ether 11-M 75.2Toluene methanol 980 Alkyl aromatic 111 3 hydrocarbon 11-N 76.8 WaterNone N/A water 100 # 11-O 74.6 Dioxane water 60 Symmetric cyclic 101 2ether 11-P 76.4 CPME methanol 1320 Symmetric cyclic 106 2 ether 11-Q75.6 MIBK methanol 1300 Asymmetric dialkyl 116 3 ketone

b. Analytical Characterization Data

XRPD

Related XRPD data is provided in FIGS. 211-227 and Tables 107-123.

TABLE 107 Peak angle data of 11-A2 (Experiment Reference 11-SampleReference A2) (Pattern #6a) Rel. Intensity 2-θ (°) d Value (%) 12.9 6.8611 16.5 5.37 71 19.4 4.58 45 19.5 4.56 100 20.6 4.32 67 22.0 4.04 2225.3 3.52 72 26.0 3.42 39 33.4 2.68 14

TABLE 108 Peak angle data of 11-B2 (Experiment Reference 11-SampleReference B2) (Pattern #6a) Rel. Intensity 2-θ (°) d Value (%) 12.9 6.8510 16.5 5.36 88 19.4 4.58 39 19.5 4.54 100 20.6 4.30 94 22.0 4.03 2225.3 3.52 76 26.0 3.42 35 33.5 2.67 13

TABLE 109 Peak angle data of 11-C2 (Experiment Reference 11-SampleReference C2) (Pattern #6a) Rel. Intensity 2-θ (°) d Value (%) 12.9 6.8513 16.5 5.38 68 19.1 4.64 23 19.5 4.56 100 20.6 4.32 69 22.0 4.04 2125.2 3.53 61 26.0 3.42 37 28.0 3.18 10 33.4 2.68 14 37.7 2.38 12

TABLE 110 Peak angle data of 11-D2 (Experiment Reference 11-SampleReference D2) (Pattern #5) Rel. Intensity 2-θ (°) d Value (%) 8.2 10.77100 9.0 9.78 26 9.7 9.09 20 11.2 7.87 46 12.8 6.92 15 14.2 6.21 11 14.56.12 17 15.0 5.90 12 15.1 5.87 11 15.5 5.71 34 16.2 5.45 51 17.0 5.20 6418.0 4.92 24 18.3 4.84 15 19.0 4.66 32 19.2 4.61 38 20.2 4.39 44 20.84.26 16 21.2 4.19 31 21.4 4.14 47 22.6 3.93 23 22.5 3.94 23 23.6 3.76 4624.3 3.66 25 25.1 3.55 13 25.5 3.49 71 26.8 3.33 18 29.9 2.98 10

TABLE 111 Peak angle data of 11-E2 (Experiment Reference 11-SampleReference E2) (Pattern #6b) 2-θ (°) d Value Rel. Intensity (%) 8.3 10.7010 13.0 6.82 20 16.5 5.35 29 19.5 4.55 100 20.6 4.30 30 22.1 4.03 1525.3 3.51 21 26.1 3.41 57

TABLE 112 Peak angle data of 11-F2 (Experiment Reference 11-SampleReference F2) (Pattern #6a) 2-θ (°) d Value Rel. Intensity (%) 12.9 6.8412 16.5 5.38 85 19.5 4.56 100 20.6 4.32 78 22.0 4.04 20 25.2 3.53 8326.0 3.42 37 33.4 2.68 15 37.7 2.38 13

TABLE 113 Peak angle data of 11-G2 (Experiment Reference 11-SampleReference G2) (Pattern #1) 2-θ (°) d Value Rel. Intensity (%) 9.1 9.7140 10.6 8.31 14 14.3 6.19 20 15.9 5.58 15 16.4 5.41 58 16.5 5.37 44 17.45.08 23 18.1 4.88 20 19.4 4.56 38 20.6 4.30 15 22.0 4.03 13 22.3 3.98 1722.6 3.94 21 25.5 3.49 64 25.6 3.48 100 26.1 3.41 14 26.8 3.32 16 27.33.27 15 30.0 2.98 16

TABLE 114 Peak angle data of 11-H2 (Experiment Reference 11-SampleReference H2) (Pattern #6a) 2-θ (°) d Value Rel. Intensity (%) 12.9 6.8514 16.5 5.37 58 19.5 4.56 100 20.6 4.31 49 22.0 4.04 14 25.3 3.52 5926.0 3.42 38 31.2 2.87 12

TABLE 115 Peak angle data of 11-I2 (Experiment Reference 11-SampleReference I2) (Pattern #6b ) 2-θ (°) d Value Rel. Intensity (%) 8.210.71 55 12.9 6.83 18 16.5 5.36 48 17.1 5.19 10 19.5 4.55 100 20.6 4.3049 22.0 4.03 12 25.3 3.52 46 26.0 3.42 41

TABLE 116 Peak angle data of 11-J2 (Experiment Reference 11-SampleReference J2) (Pattern #6a) 2-θ (°) d Value Rel. Intensity (%) 12.9 6.8415 16.5 5.36 89 19.5 4.55 99 19.5 4.55 100 20.6 4.30 84 22.0 4.03 2025.3 3.52 75 26.0 3.42 37 28.1 3.18 10 33.5 2.68 12

TABLE 117 Peak angle data of 11-K2 (Experiment Reference 11-SampleReference K2) (Pattern #5) 2-θ (°) d Value Rel. Intensity (%) 8.2 10.76100 11.3 7.86 77 12.8 6.89 15 15.5 5.70 33 17.0 5.20 59 19.1 4.64 2119.5 4.55 16 20.2 4.39 39 21.2 4.18 13 21.5 4.13 45 22.6 3.92 26 23.73.75 38 24.4 3.65 26 25.5 3.49 12 30.8 2.90 11

TABLE 118 Peak angle data of 11-L2 (Experiment Reference 11-SampleReference L2) (Pattern #6a) 2-θ (°) d Value Rel. Intensity (%) 12.9 6.8512 16.5 5.37 66 17.8 4.98 11 19.4 4.58 61 19.5 4.56 100 20.6 4.31 9522.0 4.04 15 25.3 3.52 71 26.0 3.42 55 28.0 3.18 13 33.4 2.68 14 39.62.28 15

TABLE 119 Peak angle data of 11-M2 (Experiment Reference 11-SampleReference M2) (Pattern #6a) 2-θ (°) d Value Rel. Intensity (%) 8.4 10.4911 11.2 7.91 13 12.5 7.09 11 12.9 6.85 12 14.4 6.14 11 16.5 5.36 10016.9 5.24 22 18.8 4.73 16 19.2 4.62 22 19.5 4.55 81 20.1 4.41 27 20.64.31 60 22.1 4.02 18 22.2 4.00 21 25.3 3.52 53 25.6 3.47 18 26.1 3.42 5326.7 3.34 12 33.4 2.68 12

TABLE 120 Peak angle data of 11-N2 (Experiment Reference 11-SampleReference N2) (Pattern #6a) 2-θ (°) d Value Rel. Intensity (%) 13.0 6.8015 16.6 5.33 71 19.6 4.53 100 20.7 4.29 50 22.1 4.01 22 25.4 3.51 5026.1 3.41 38 33.6 2.67 11

TABLE 121 Peak angle data of 11-O2 (Experiment Reference 11-SampleReference O2) (Pattern #6a) 2-θ (°) d Value Rel. Intensity (%) 7.5 11.8014 12.9 6.86 11 15.9 5.58 13 16.5 5.37 63 19.5 4.56 100 20.6 4.31 5122.0 4.04 21 25.3 3.52 51 26.0 3.42 42 33.4 2.68 13

TABLE 122 Peak angle data of 11-P2 (Experiment Reference 11-SampleReference P2) (Pattern #5) 2-θ (°) d Value Rel. Intensity (%) 8.2 10.77100 11.3 7.85 51 12.8 6.90 15 15.5 5.70 43 16.3 5.43 15 17.0 5.20 6419.1 4.64 31 19.4 4.56 16 20.2 4.39 47 20.6 4.32 12 21.3 4.16 33 21.54.13 77 22.7 3.92 26 23.7 3.75 53 24.3 3.65 15 25.5 3.49 29 26.0 3.42 1130.8 2.90 11

TABLE 123 Peak angle data of 11-Q2 (Experiment Reference 11-SampleReference Q2) (Pattern #14) 2-θ (°) d Value Rel. Intensity (%) 8.2 10.7189 11.3 7.82 100 12.9 6.88 14 15.6 5.69 25 16.3 5.43 16 17.1 5.19 5619.1 4.63 13 20.3 4.38 35 21.3 4.17 13 21.5 4.12 37 22.7 3.91 36 23.73.75 37 24.4 3.65 10 25.5 3.48 27 30.8 2.90 11

c. Conclusion

Crystallization from different solvents can be a useful method toinvestigate alternative polymorphic forms. This crystallization screenof the tabernanthalog monofumarate salt could also be used to identifypotential conditions for scale-up crystallizations to control the formoutcome. XRPD analysis of the final products showed Patterns #1, #5, #6aand #6b. Evidently, in the presence of water, Patterns #6a and #6b weredelivered (refer to Table 124). Apart from 11-E (Experiment Reference11-Sample Reference E) were DCM and methanol were used.

TABLE 124 Summary for HUCD crystallization experiment Experiment Co-Reference- Input solvents Sample Input weights (volumes Key chemicalb.p. ICH Reference reference (mg) Solvent A Solvent B added, μl)functional groups (° C.) Classes 11-A Tabernanthalog 74.7 Acetone water80 Symmetrical 56 3 fumarate ketone 11-B Sample 76.9 Acetonitrile water120 Simple dipolar- 82 2 Reference aprotic nitrile 11-C 1 77.6 Butanolwater 60 Linear aliphatic 118 3 alcohol 11-D 76.7 tert-Butylmethylmethanol 2800 Branched aliphatic 55 3 ether methoxyether 11-E 75.7Dichloromethane methanol 880 Chlorinated 40 2 hydrocarbon 11-F 77.2Ethanol water 60 Linear aliphatic 78 3 alcohol 11-G 76.0 methyl acetatewater / 80 Aliphatic ester 57 3 methanol 11-H 76.3 2-Propanol water 80Branched aliphatic 83 3 alcohol 11-1 77.4 methanol None N/A Linearaliphatic 65 3 alcohol 11-J 76.2 Methylethyl water 60 Asymmetric dialkyl80 3 ketone ketone 11-K 75.5 2-Methyl THF methanol 1560 Asymmetriccyclic 80 3 ether 11-L 74.8 Tetrahydrofuran water 60 Symmetric cyclic 80# ether 11-M 75.2 Toluene methanol 980 Alkyl aromatic 111 3 hydrocarbon11-N 76.8 Water None N/A water 100 # 11-O 74.6 Dioxane water 60Symmetric cyclic 101 2 ether 11-P 76.4 CPME methanol 1320 Symmetriccyclic 106 2 ether 11-Q 75.6 MIBK methanol 1300 Asymmetric dialkyl 116 3ketone Summary for HUCD crystallization experiment Experiment Reference-Observations Sample (t = 0 @ XRPD (oven Yield Reference T = 20° C.)dried Tare Gross Net % 11-A suspension Pattern #6a 1.0071 1.028 0.020928.0% 11-B cloudy Pattern #6a 1.0039 1.0394 0.0355 46.2% 11-C suspensionPattern #6a 1.0024 1.0457 0.0433 55.8% 11-D cloudy Pattern #5 1.00071.0271 0.0264 34.4% 11-E suspension Pattern #6b 1.0027 1.0508 0.048163.5% 11-F suspension Pattern #6a 1.0035 1.0401 0.0366 47.4% 11-Gsuspension Pattern #1 1.0008 1.0289 0.0281 37.0% 11-H cloudy Pattern #6a1.0026 1.0404 0.0378 49.5% 11-1 suspension Pattern #6b 1.0051 1.06330.0582 75.2% 11-J suspension Pattern #6a 1.0043 1.0436 0.0393 51.6% 11-Ksuspension Pattern #5 0.9988 1.0312 0.0324 42.9% 11-L solution Pattern#6a 1.0119 1.0287 0.0168 22.5% 11-M suspension Pattern #6b 1.0171 1.05680.0397 52.8% 11-N suspension Pattern #6a 1.0032 1.0542 0.051 66.4% 11-Osuspension Pattern #6a 1.0052 1.0253 0.0201 26.9% 11-P suspensionPattern #5 1.0102 1.036 0.0258 33.8% 11-Q solution Pattern #5 1.00791.0457 0.0378| 50.0%

x. Mechanochemistry (LAG) (Experiment Reference 12)

a. Experimental Procedure

The tabernanthalog monofumarate salt (Pattern #1, Sample Reference 1, 75mg) and one ball-bearing (7.0 mm, 1.4 g) were placed inside a steelvessel (1.5 ml), and attached to a Retsch MM 500, VARIO mixer-mill.

The vessel was oscillated at 500 rpm for 30 minutes, under neat grindingcondition (NG, suffix -A) and liquid assisted grinding condition (LAG,methanol η=0.5, suffix -B).

b. Analytical Characterization Data

DSC

DSC results are provided in FIGS. 228 and 229 .

XRPD

XRPD results are provided in FIGS. 230 and 231 and Tables 125 and 126.

TABLE 125 Peak angle data of 12-A1 (Experiment Reference 12-SampleReference A1) 2-θ (°) d Value Rel. Intensity (%) 6.8 12.98 13 9.2 9.6530 14.3 6.18 15 16.4 5.39 90 16.8 5.27 35 17.6 5.05 15 17.9 4.95 16 18.24.87 32 18.9 4.69 14 19.4 4.57 41 22.2 4.00 11 22.4 3.96 21 23.2 3.83 1325.6 3.47 100 26.3 3.39 12 26.9 3.31 26 27.3 3.27 22

TABLE 126 Peak angle data of 12-B1 (Experiment Reference 12-SampleReference B1) 2-θ (°) d Value Rel. Intensity (%) 8.2 10.74 44 9.1 9.7625 11.2 7.88 27 12.8 6.90 12 14.2 6.22 13 15.5 5.71 21 16.3 5.42 82 17.05.20 39 18.1 4.91 16 19.3 4.60 18 19.5 4.55 26 20.2 4.39 26 20.6 4.30 1721.5 4.14 27 21.5 4.13 29 22.0 4.04 10 22.6 3.94 22 22.6 3.93 23 23.73.75 28 25.6 3.48 100 26.0 3.43 15 26.8 3.32 22 27.2 3.28 14 30.0 2.9811

c. Conclusion

Both pulverization conditions, appeared to promote incomplete conversioninto the stable form identified as 6-S2 (Experiment Reference 6-SampleReference S2), Pattern #6a (provided below). DSC thermograms under neatgrinding (NG, 12-A1 (Experiment Reference 12-Sample Reference A1)) andunder liquid assisted grinding conditions (LAG, 12-B1 (ExperimentReference 12-Sample Reference B1)) are presented in FIG. 232 . XRPDdiffractograms under neat grinding (NG, black, 12-A1 (ExperimentReference 12-Sample Reference A1), Pattern #6a, top right) and underliquid assisted grinding conditions (LAG, black, 12-B1 (ExperimentReference 12-Sample Reference B1), Pattern #6a, bottom, right) arepresented in FIG. 233 .

xi. Vapour diffusion (Experiment Reference 13)

a. Experimental Procedure

The tabernanthalog monofumarate salt (Sample Reference 1, Pattern #1,3×75 mg, 1 wt) was weighed out in to 3 separate snap-top vials and DMSO(375 ul, 5 vol) was charged to each vial. Gentle warning was applied toensure full dissolution and the vials (open) were placed inside amberjars that contained 6 ml of DCM (13-A) (Experiment Reference 13-SampleReference A), tBME (13-B) (Experiment Reference 13-Sample Reference B)and water (13-C) (Experiment Reference 13-Sample Reference C).

The 3 jars that contained the vials were left standing at 20° C., toallow slow movement of the diffusant solvent from the outer jar into thesolvent inside the smaller, open wide-necked vessel and promotecrystallization by altering the solvent composition.

b. Analytical Characterization Data

¹H NMR

Relevant NMR spectra are provided in FIGS. 234 and 235 .

TGA

Relevant TGA profiles are provided in FIGS. 236 and 237 .

DSC

Relevant DSC profiles are provided in FIGS. 238 and 239 .

XRPD

XRPD results are provided in FIGS. 240-243 and Table 127-130.

TABLE 127 Peak angle data of 13-B1 (Experiment Reference 13-SampleReference B1) (Pattern #24) 2-θ (°) d Value Rel. Intensity (%) 12.4 7.1619 15.7 5.63 31 16.1 5.50 25 16.7 5.29 14 17.2 5.16 100 20.1 4.41 1320.8 4.27 37 21.1 4.20 22 21.6 4.11 19 22.3 3.99 28 23.0 3.86 39 24.93.57 20 27.4 3.25 40

TABLE 128 Peak angle data of 13-B2 (Experiment Reference 13-SampleReference B2) (Pattern #24) 2-θ (°) d Value Rel. Intensity (%) 12.2 7.2220 15.6 5.66 39 15.9 5.56 25 17.0 5.20 100 20.7 4.29 32 21.0 4.23 2221.5 4.13 15 22.9 3.88 38 24.8 3.59 19 27.3 3.26 30

TABLE 129 Peak angle data of 13-C1 (Experiment Reference 13-SampleReference C1) (Pattern #23) 2-θ (°) d Value Rel. Intensity (%) 12.9 6.8572 15.0 5.90 11 16.1 5.51 47 17.1 5.19 33 17.8 4.99 100 18.8 4.72 1220.5 4.32 26 20.9 4.24 29 21.6 4.12 44 22.3 3.99 15 23.0 3.87 98 23.23.83 20 25.0 3.56 20 25.7 3.47 61 26.8 3.32 28 27.4 3.25 69 28.1 3.18 1438.9 2.31 12

TABLE 130 Peak angle data of 13-C2 (Experiment Reference 13-SampleReference C2) (Pattern #23) 2-θ (°) d Value Rel. Intensity (%) 12.2 7.2512 12.8 6.90 40 14.9 5.94 11 16.0 5.54 39 16.2 5.45 23 16.9 5.24 24 17.65.02 100 20.4 4.35 19 20.8 4.27 22 21.4 4.14 30 22.9 3.89 76 23.1 3.8516 25.6 3.48 36 26.7 3.33 19 27.3 3.27 39

PLM

PLM results are provided in FIGS. 244-247 .

c. Conclusion

Vapour diffusion is a slower thermodynamic crystallization technique andgood for generating single crystals suitable for SCXRD. It involved asolution of the tabernanthalog monofumarate salt in the relevantnon-diffusant solvent (DMSO was used due to the inherent low solubilityof the tabernanthalog monofumarate salt), being placed inside a small,wide-necked vessel. The wide-necked vessel was then placed inside alarger jar, and the appropriate diffusant solvent (DCM, tBME and waterwere used. Water was included as one of the diffusant solvents, to tryand generate crystals suitable for SCXRD) was added to the jar, to forma moat of diffusant around the smaller vessel (FIG. 248 ).

As the diffusant solvent gradually evaporated, the composition of thenon-diffusant solvent changed and in doing so, promotedde-supersaturation and crystallization of the tabernanthalogmonofumarate salt. (13-A) (Experiment Reference 13-Sample Reference A)remained in full solution, and (13-A) (Experiment Reference 13-SampleReference A) and (13-B) (Experiment Reference 13-Sample Reference B) didnot appear to give suitable crystals for SCXRD (refer to Table 131).Microscopy showed that (13-B) (Experiment Reference 13-Sample ReferenceB) had much larger single crystals than (13-C) (Experiment Reference13-Sample Reference C). Both samples showed large amounts ofaggregation.

TABLE 131 Summary of vapour diffusion experiment crystal Co- XRPD formExperiment solvents crystal- change ¹H NMR Reference- Input Solvent(volumes XRPD linity follow- (solvent Sample Input weights A Solventadded, crystallinity (oven ing Tare Gross Net Yield content, Referencereference (mg) (5 vol) B μL) (wet pellet) dried) dry (mg) (mg) (mg) % %w/w) 13-A Sample 75.1 DMSO DCM 6.0 OP 1019.2 Reference 13-B 1 75.1 DMSOTBME 6.0 Pattern #24 Pattern #24 O 1000.7 1017.7 17.0 22 DMSO = (v. (v.1.14 disordered) disordered) 13-C 75.5 DMSO Water 6.0 Pattern #23Pattern #23 O 999.8 1019.5 19.7 26 DMSO = (v. (v. 0.78 disordered)disordered)

xii. Evaporation Screen (Experiment Reference 14)

a. Experimental Procedure

Crystallization of the API was examined by changing the composition ofthe crystallization solvent by evaporation of a volatile diluent. Thistechnique is useful for generating kinetic forms and solvates. Separateportions of the tabernanthalog monofumarate salt (Pattern #1, SampleReference 1, ca 50 mg, 1.0 wt.) were charged to separate vessels. DMSO(100 μl, 2.0 vol, refer to Table 132) was charged to the relevantvessels and subsequent charges of the appropriate co-solvent (900 μl,18.0 vol) were made to accomplish dissolution. The vials were coveredwith an aluminum foil cap and pierced with a single hole, then left tostand at 20° C. After 6 days, gentle nitrogen flux was applied todryness. The products were analyzed by XRPD and companion analyses, forevidence of alternative crystalline forms.

TABLE 132 Evaporation screen setup description Experiment Reference-Input Solvent Co-solvents Sample Input weights Solvent A volume SolventB volumes Reference reference (m g) (1 vol) added (mL) (19 vol) added(mL) 14-A Sample Reference 51.0 DMSO 0.1 EtOH 0.9 14-B 1 49.2 DMSO 0.1nBuOH 0.9 14-C 50.2 DMSO 0.1 Water 0.9

b. Analytical Characterization Data

¹H NMR

Relevant NMR spectra are provided in FIGS. 249-251 .

TGA

Relevant TGA profiles are provided in FIGS. 252-254 .

XRPD

Relevant XRPD profiles are provided in FIGS. 255-260 and Tables 133−138.

TABLE 133 Peak angle data of 14-A1 (Experiment Reference 14-SampleReference A1) (wet sample, disordered Pattern #23) 2-θ (°) d Value Rel.Intensity (%) 7.8 11.34 11 12.4 7.14 15 13.0 6.82 44 13.0 6.78 31 15.05.89 12 16.1 5.49 35 16.4 5.39 18 16.7 5.30 24 17.2 5.16 23 17.8 4.98 7818.4 4.82 13 19.6 4.53 38 19.7 4.51 100 20.9 4.25 41 21.6 4.11 33 22.33.98 31 23.0 3.86 66 23.3 3.82 18 25.6 3.48 30 26.1 3.41 22 26.3 3.39 4926.9 3.32 18 27.5 3.24 33 28.1 3.17 11

TABLE 134 Peak angle data of 14-A2 (Experiment Reference 14-SampleReference A2) (oven dried sample, Pattern #23) 2-θ (°) d Value Rel.Intensity (%) 7.7 11.50 11 12.2 7.28 12 12.8 6.93 24 14.9 5.96 12 15.95.56 32 16.2 5.46 26 16.5 5.38 22 16.8 5.26 21 17.6 5.04 100 19.4 4.5627 20.4 4.35 17 20.7 4.30 23 21.4 4.15 28 22.1 4.02 12 22.8 3.89 64 23.13.85 13 25.4 3.50 22 25.5 3.49 26 26.7 3.34 16 27.2 3.27 34 27.9 3.20 11

TABLE 135 Peak angle data of 14-B1 (Experiment Reference 14-SampleReference B1) (wet sample, disordered Pattern #23) 2-θ (°) d Value Rel.Intensity (%) 7.7 11.45 27 12.3 7.19 15 12.8 6.92 48 15.7 5.64 31 16.05.55 32 16.3 5.45 20 17.0 5.20 60 17.6 5.02 100 20.7 4.28 39 21.0 4.2248 21.5 4.14 45 22.9 3.88 71 24.9 3.57 56 25.5 3.49 91 26.7 3.33 42 27.33.26 46

TABLE 136 Peak angle data of 14-B2 (Experiment Reference 14-SampleReference B2) (oven dried sample, Pattern #23) 2-0 (º) d Value Rel.Intensity (%) 12.2 7.22 12 12.9 6.88 32 16.0 5.52 37 16.3 5.43 39 16.95.23 20 17.7 5.01 100 20.4 4.34 17 20.8 4.26 18 21.5 4.13 23 22.2 4.0011 22.9 3.88 61 23.1 3.84 13 25.6 3.48 34 26.8 3.33 17 27.3 3.26 29

TABLE 137 Peak angle data of 14-C1 (Experiment Reference 14-SampleReference C1) (wet sample, high background Pattern #6a) 2-θ (°) d ValueRel. Intensity (%) 13.0 6.79 14 16.6 5.33 17 17.1 5.17 20 19.6 4.53 10020.8 4.27 31 22.2 4.01 10 23.0 3.86 13 25.4 3.50 17 26.2 3.40 58 27.53.25 11

TABLE 138 Peak angle data of 14-C2 (Experiment Reference 14-SampleReference C2) (oven dried sample, Pattern #6a) 2-θ (°) d Value Rel.Intensity (%) 13.0 6.83 24 16.5 5.35 44 17.0 5.20 10 19.4 4.58 18 19.54.55 100 20.7 4.30 44 22.1 4.02 21 25.3 3.51 37 26.1 3.41 61

Photography

Photography results are shown in FIGS. 261-263 .

c. Conclusion

An evaporation screen of the tabernanthalog monofumarate salt wasperformed to determine if alternative polymorphic forms were generatedby evaporative crystallization from different solvents. XRPD resultsshowed much higher crystallinity following oven dry (FIGS. 264-266 ) andTGA showed no solvent release. Table 139 presents a summary ofevaporation screen experiment.

TABLE 139 Summary of evaporation screen experiment Experiment SolventReference- Input volume Co-solvents XRPD XRPD Sample Input weightsSolvent A added Solvent B volumes crystallinity crystallinity Yield ¹HNMR (solvent Reference reference (mg) (1 vol) (mL) (19 vol) added(mL)(wet pellet) (oven dried) % content, % w/w) 14-A Sample Reference 51.0DMSO 0.1 EtOH 0.9 Disordered Pattern 23 37.5 DMSO = 0.75 1 (Pattern #23)Ethanol ND 14-B 49.2 DMSO 0.1 nBuOH 0.9 Disordered Pattern 23 64.2 DMSO= 0.91 (Pattern #23) Butanol ND 14-C 50.2 DMSO 0.1 Water 0.9 HighPattern 6a 91.2 DMSO = 2.21 background (Pattern #6a)

xiii. In-Situ Hydration Evaluation (Experiment Reference 15)

a. Experimental Procedure

An XRPD plate was made up with a small amount of the tabernanthalogmonofumarate salt (Pattern #1, Sample Reference 1, 5 mg, 1.0 wt) andanalyzed by XRPD on the 9-minute method and labelled as T=0. After therun, the sample was charged with purified water (10 μL, 2.0 vol) andanalyzed again by XRPD, labelled as T=9. This was repeated twice morefor T=18 and T=27. The sample was left to stand under ambient conditions(15-25° C., ambient humidity, and pressure) in the fume hood for 33 hand then analyzed by XRPD.

b. Analytical Characterization Data

XRPD

XRPD results are shown in FIGS. 267-271 and Tables 140-143.

TABLE 140 Peak angle data of 15-T0 (Experiment Reference 15-SampleReference T0) (Pattern #1, Sample Reference 1) 2-θ (°) d Value Rel.Intensity (%) 9.1 9.72 27 14.2 6.21 13 16.4 5.42 74 16.7 5.30 29 17.55.07 12 17.7 5.00 10 18.1 4.89 29 19.3 4.59 34 22.3 3.98 24 22.5 3.95 1123.1 3.84 11 25.2 3.53 18 25.6 3.48 100 26.2 3.40 13 26.8 3.32 25 27.33.27 24 28.7 3.11 11 30.0 2.98 11

TABLE 141 Peak angle data of 15-T9 (Experiment Reference 15-SampleReference T9) (amorphousised Pattern #1) 2-θ (°) d Value Rel. Intensity(%) 9.1 9.70 13 14.3 6.20 11 16.4 5.41 65 17.5 5.07 13 18.1 4.90 17 22.33.98 14 25.1 3.54 15 25.6 3.48 100 26.8 3.33 24 27.2 3.28 16 29.9 2.9814

TABLE 142 Peak angle data of 15-T27 (Experiment Reference 15-SampleReference T27) (amorphousised Pattern #1) 2-θ (°) d Value Rel. Intensity(%) 6.8 13.06 11 9.1 9.68 31 14.3 6.20 15 16.4 5.41 80 16.7 5.31 24 18.14.89 19 19.4 4.58 16 22.4 3.96 19 25.2 3.53 25 25.6 3.48 100 26.8 3.3225 27.2 3.27 17 28.1 3.17 11 28.6 3.12 16 30.0 2.98 19

TABLE 143 Peak angle data of 15-T33 (Experiment Reference 15-SampleReference T33) (amorphized Pattern #1) 2-θ (°) d Value Rel. Intensity(%) 6.8 13.03 16 9.1 9.68 43 14.3 6.19 18 15.1 5.88 6 16.2 5.46 18 16.45.39 100 16.8 5.26 34 17.5 5.06 19 17.9 4.96 15 18.2 4.87 21 18.9 4.6913 19.4 4.57 33 22.4 3.96 17 24.9 3.57 12 25.4 3.51 84 25.7 3.47 61 26.63.34 19 26.8 3.32 16

c. Conclusion

The overlaid XRPD results indicate that the same crystal form isrecovered following hydration and subsequent drying (FIG. 272 ). xiv.Competitive suspension equilibration (Form A and Form B) (ExperimentReference 16) a. Experimental Procedure Equimolar quantities of Form A(Pattern #6a, 25.4 mg, 1 wt, 8-A4; (Experiment Reference 8-SampleReference A4)) and Form B (Pattern #2a, 25.0 mg, 1 wt, Sample B-A2) weresuspended in tBME (250 μl, 5.0 vol). The first experiment was agitatedat 20° C., (16-A) (Experiment Reference 16-Sample Reference A), whilethe other was agitated at 40° C. (16-B) (Experiment Reference 16-SampleReference B). The suspension was monitored by XRPD analysis.

b. Analytical Characterization Data

XRPD

XRPD results are provided in FIGS. 273-282 and Tables 144-153.

TABLE 144 Peak angle data of 16-A1 (Experiment Reference 16-SampleReference A1) (wet sample, t = 24 h) 2-θ (°) d Value Rel. Intensity (%)9.1 9.74 24 12.2 7.22 24 14.2 6.22 12 15.7 5.65 32 15.9 5.57 17 16.45.41 92 16.5 5.36 49 17.0 5.20 63 18.1 4.91 23 19.5 4.54 56 20.7 4.30 6421.0 4.23 18 22.1 4.02 15 22.9 3.88 28 24.9 3.57 13 25.6 3.48 100 26.13.41 19 26.8 3.33 22 27.3 3.26 27

TABLE 145 Peak angle data of 16-A2 (Experiment Reference 16-SampleReference A2) (wet sample, t = 48 h) 2-θ (°) d Value Rel. Intensity (%)9.0 9.77 19 12.2 7.24 18 12.9 6.85 12 14.2 6.23 12 15.7 5.66 26 15.95.58 17 16.4 5.41 75 16.5 5.38 82 17.0 5.20 41 17.9 4.94 12 18.0 4.92 1418.7 4.74 10 19.5 4.55 100 20.6 4.30 88 20.9 4.25 13 22.0 4.03 21 22.93.88 18 24.8 3.58 11 25.4 3.51 73 25.5 3.49 66 26.0 3.42 29 26.7 3.33 1427.3 3.27 16 33.5 2.68 10

TABLE 146 Peak angle data of 16-A3 (Experiment Reference 16-SampleReference A3) (wet sample, t = 108 h) 2-θ (°) d Value Rel. Intensity (%)9.1 9.76 21 12.2 7.23 19 12.9 6.84 12 14.2 6.23 12 15.7 5.65 23 16.45.39 75 16.5 5.37 82 17.0 5.20 41 18.0 4.92 16 19.5 4.55 100 20.6 4.3087 21.0 4.24 11 22.0 4.03 21 22.9 3.88 17 25.4 3.51 68 25.5 3.49 59 26.13.42 32 26.8 3.33 16 27.3 3.26 14 33.5 2.68 11

TABLE 147 Peak angle data of 16-A4 (Experiment Reference 16-SampleReference A4) (wet sample, t = 192 h) 2-θ (°) d Value Rel. Intensity (%)9.1 9.71 17 12.3 7.20 16 13.0 6.82 14 15.7 5.63 21 16.5 5.36 87 17.15.19 30 18.1 4.90 21 19.5 4.54 100 20.7 4.29 77 22.1 4.02 21 23.0 3.8717 25.4 3.50 67 25.5 3.48 55 26.1 3.41 30 26.8 3.32 13 26.8 3.32 11 27.43.26 13 33.5 2.67 10

TABLE 148 Peak angle data of 16-A8 (Experiment Reference 16-SampleReference A8) (wet sample, t = 4 weeks) 2-θ (°) d Value Rel. Intensity(%) 12.2 7.23 11 12.9 6.83 14 16.6 5.34 96 16.5 5.36 96 17.1 5.19 2017.8 4.97 19 18.1 4.91 30 18.8 4.73 12 19.5 4.54 100 20.7 4.30 76 22.14.03 18 22.9 3.88 11 25.4 3.51 66 25.5 3.49 46 26.1 3.41 28

TABLE 149 Peak angle data of 16-B1 (Experiment Reference 16-SampleReference B1) (wet sample, t = 24 h) 2-θ (°) d Value Rel. Intensity (%)9.1 9.73 16 12.2 7.22 14 13.0 6.83 14 15.7 5.65 25 15.9 5.56 12 16.55.36 76 17.1 5.19 38 18.0 4.91 16 18.8 4.72 10 19.5 4.55 100 20.7 4.3075 21.0 4.24 11 22.1 4.03 23 22.9 3.88 18 25.4 3.50 57 25.5 3.49 53 26.13.42 36 26.8 3.33 13 27.3 3.26 14

TABLE 150 Peak angle data 16-B2 (Experiment Reference 16-SampleReference B2) (wet sample, t = 48 h) 2-θ (°) d Value Rel. Intensity (%)9.1 9.75 15 12.2 7.22 14 12.9 6.84 15 15.7 5.65 22 16.5 5.37 63 17.05.20 31 18.0 4.91 15 19.5 4.55 100 20.6 4.30 56 20.9 4.24 13 22.1 4.0321 22.9 3.88 14 25.4 3.50 50 26.1 3.42 44 27.3 3.26 12 33.5 2.68 11

TABLE 151 Peak angle data of 16-B3 (Experiment Reference 16-SampleReference B3) (wet sample, t = 108 h) 2-θ (°) d Value Rel. Intensity (%)9.0 9.76 13 12.2 7.24 13 12.9 6.85 12 14.2 6.23 10 15.7 5.66 19 16.45.41 55 16.5 5.38 72 17.0 5.20 29 18.0 4.92 20 19.5 4.56 100 20.6 4.3170 20.8 4.26 14 22.0 4.03 22 22.9 3.88 19 25.3 3.51 54 25.5 3.49 46 26.03.42 36 26.7 3.33 13 27.3 3.27 11 33.4 2.68 10

TABLE 152 Peak angle data of 16-B4 (Experiment Reference 16-SampleReference B4) (wet sample, t = 192 h) 2-θ (°) d Value Rel. Intensity (%)12.3 7.18 10 13.0 6.78 12 15.8 5.59 15 16.6 5.33 68 17.1 5.17 21 17.84.98 19 18.1 4.91 35 18.8 4.71 10 19.6 4.53 100 20.7 4.28 54 22.1 4.0124 23.0 3.86 13 25.4 3.50 53 26.2 3.40 41

TABLE 153 Peak angle data of 16-B8 (Experiment Reference 16-SampleReference B8) (wet sample, t = 4 weeks) 2-θ (°) d Value Rel. Intensity(%) 13.0 6.78 10 12.9 6.84 16 16.1 5.52 12 16.5 5.35 85 17.0 5.22 1117.7 5.01 32 18.0 4.91 44 19.5 4.55 100 20.7 4.29 62 22.1 4.02 21 22.93.88 18 25.4 3.51 61 26.1 3.41 32 26.7 3.34 11 33.5 2.67 10

c. Conclusion

Competitive suspension equilibration of Form A (8-A4) (ExperimentReference 8-Sample Reference A4) versus Form B (Sample B-A2) wasperformed at 20° C. ((16-A; Experiment Reference 16-Sample Reference A)and 40° C. ((16-B; Experiment Reference 16-Sample Reference B) in tBME(5.0 vol) to verify that Form A (Pattern #6a) is more stable. The outputof the suspension was monitored by XRPD analysis and overlaid with thetwo inputs to confirm the conversion towards Form A. The stacked XRPDtimepoints were consistent with gradual transformation of Form B(Pattern #2a) into Form A (Pattern #6a) in both experiments, supportingthe relative stability of succession Form A>Form B ((FIG. 283 and FIG.284 ). At the end of the experiment, Form A was the dominant form,therefore the stable one. Summary of competitive suspensionequilibration between Form A and Form B (16-A (Experiment Reference16-Sample Reference A) and 16-B (Experiment Reference 16-SampleReference B)) is provided in Table 153A.

TABLE 153A Summary of competitive suspension equilibration between FormA and Form B (16-A and 16-B). More time points were examined between 192h and 4 weeks; however, they were very similar with 16-A4 (ExperimentReference 16-Sample Reference A4) an 16-B4 (Experiment Reference16-Sample Reference B4), respectively. Input Input weights XRPDReferences reference (mg) Solvent T (° C.) (24 h, -A1) 16-A 8-A4 25.4(Form A) TBME 20 Form A > Form B 16-B (Form A) and and 25.0 (5.0 vol) 40Form A > Form B Sample B-A2 (Form B) (Form B) Summary of competitivesuspension equilibration between Form A and Form B (16-A and 16-B). Moretime points were examined between 192 h and 4 weeks; however, they werevery similar with 16-A4 (Experiment Reference 16-Sample Reference A4) an16-B4 (Experiment Reference 16-Sample Reference B4), respectively. XRPDXRPD XRPD XRPD References (48 h, -A2) (108 h, -A3) (192 h, -A4) (4weeks, -A8) 16-A Form A > Form B Form A > Form B Form A >> Form B FormA > Form B 16-B Form A > Form B Form A > Form B Form A >> Form B FormA > Form B

xiv. SCXRD (Single crystal (SC) experiments)

a. Experimental Procedure

A crystalline sample of 11-M2 (Experiment Reference 11-Sample ReferenceM2) and 11-Q2 (Experiment Reference 11-Sample Reference Q2), which wereused as supplied, was isolated. A small portion of this sample wassuspended in perfluoro ether oil and a suitable colorless block-shapedcrystal with dimensions 0.13×0.05×0.03 mm³ was selected. This crystalwas mounted on a MITIGEN holder in perfluoro ether oil on a Rigaku 007HFdiffractometer with HF Varimax confocal mirrors, an UG2 goniometer andHyPix 6000HE detector. The crystal was kept at a steady T=300(2) Kduring data collection. The structure was solved with the ShelXT 2014/5(Sheldrick, 2014) solution program using dual methods and by using Olex21.5 (Dolomanov et al., 2009) as the graphical interface. The model wasrefined with ShelXL 2014/7 (Sheldrick, 2015) using full matrix leastsquares minimisation on F^(2.)

11-M2 (Experiment Reference 11-Sample Reference M2): X-ray data werecollected upon a colorless block-shaped crystal with dimensions0.13×0.05×0.03 mm³, which was mounted on a MITIGEN holder in perfluoroether oil. X-ray diffraction data were collected using a Rigaku 007HFdiffractometer with HF Varimax confocal mirrors, an UG2 goniometer andHyPix 6000HE detector equipped with an Oxford Cryosystemslow-temperature device, operating at T=300(2) K.

Data were measured using profile data from ω-scans of 0.5° per frame for3.0/12.0 s using Cu K α radiation (Rotating anode, 40.0 kV, 30.0 mA).The total number of runs and images was based on the strategycalculation from the program CrysAlisPro 1.171.42.51a (Rigaku OD, 2022).The maximum resolution achieved was θ=76.907°.

Cell parameters were retrieved using the CrysAlisPro 1.171.42.51a(Rigaku OD, 2022) software and refined using CrysAlisPro 1.171.42.51a(Rigaku OD, 2022) on 14613 reflections, 44% of the observed reflections.Data reduction was performed using the CrysAlisPro 1.171.42.51a (RigakuOD, 2022) software which corrects for Lorentz polarisation. The finalcompleteness is 100.00% (IUCr) out to 76.907° in θ

A multi-scan absorption correction was performed using CrysAlisPro1.171.42.51a (Rigaku Oxford Diffraction, 2022) Empirical absorptioncorrection using spherical harmonics, implemented in SCALE3 ABSPACKscaling algorithm. The absorption coefficient m of this material is0.801 mm⁻¹ at this wavelength (λ=1.54184 Å) and the minimum and maximumtransmissions are 0.696 and 1.000.

The structure was solved in the space group P2_(1/c) (#14) by using dualmethods using the ShelXT 2014/5 (Sheldrick, 2014) structure solutionprogram and refined by full matrix least squares minimisation on P usingversion 2014/7 of ShelXL 2014/7 (Sheldrick, 2015). All non-hydrogenatoms were refined anisotropically. The positions of the N—H atoms H1and H2 and the O—H atom H4 were located from the electron difference mapand refined with their thermal parameters linked to their parent atoms.The positions of the remaining H atoms were calculated geometrically andrefined using the riding model.

There is a single molecule in the asymmetric unit, which is representedby the reported sum formula. In other words: Z is 4 and Z′ is 1. 11-Q2(Experiment Reference 11-Sample Reference Q2): X-ray data were collectedupon a yellow rod-shaped crystal with dimensions 0.10×0.03×0.01 mm³,which was mounted on a MITIGEN holder in perfluoro ether oil. X-raydiffraction data were collected using a Rigaku 007HF diffractometer withHF Varimax confocal mirrors, an UG2 goniometer and HyPix 6000HE detectorequipped with an Oxford Cryosystems low-temperature device, operating atT=300(2) K.

Data were measured using profile data from ω-scans of 0.5° per frame for9.0/36.0 s using Cu K α radiation (Rotating anode, 40.0 kV, 30.0 mA).The total number of runs and images was based on the strategycalculation from the program CrysAlisPro 1.171.42.51a (Rigaku OD, 2022).The maximum resolution achieved was θ=77.152°.

Cell parameters were retrieved using the CrysAlisPro 1.171.42.51a(Rigaku OD, 2022) software and refined using CrysAlisPro 1.171.42.51a(Rigaku OD, 2022) on 2649 reflections, 23% of the observed reflections.Data reduction was performed using the CrysAlisPro 1.171.42.51a (RigakuOD, 2022) software which corrects for Lorentz polarisation. The finalcompleteness is 98.1000 (IUCr) out to 77.152° in θ.

A multi-scan absorption correction was performed using CrysAlisPro1.171.42.51a (Rigaku Oxford Diffraction, 2022) Empirical absorptioncorrection using spherical harmonics, implemented in SCALE3 ABSPACKscaling algorithm. The absorption coefficient m of this material is0.680 mm⁻¹ at this wavelength (λ=1.54184 Å) and the minimum and maximumtransmissions are 0.733 and 1.000.

The structure was solved in the space group C2/c (#15) by using dualmethods using the ShelXT 2014/5 (Sheldrick, 2014) structure solutionprogram and refined by full matrix least squares minimisation on F²using version 2014/7 of ShelXL 2014/7 (Sheldrick, 2015). Allnon-hydrogen atoms were refined anisotropically. The positions of theN—H atoms H1 and H2 and the O—H atom H4 were located from the electrondifference map and refined with their thermal parameters linked to theirparent atoms. The positions of the remaining H atoms were calculatedgeometrically and refined using the riding model.

The value of Z′ is 2. This means that there are two independentmolecules in the asymmetric unit.

b. Analytical Characterization Data

Crystal data for 11-M2 (Experiment Reference 11-Sample Reference M2) andCrystal data for 11-Q2 (Experiment Reference 11-Sample Reference Q2) areprovided in FIGS. 285 and 286 , respectively.

c. Conclusion

(i) SCXRD Form A (Pattern #6a)

The crystalline tabernanthalog monofumarate (Pattern #6a) ischaracterized by XRPD signals as forth in Table 119.

Crystal Data for 11-M2 (Experiment Reference 11-Sample Reference M2)(FIG. 287 ). C₁₈H₂₂N₂O₅, M_(r)=346.37, monoclinic, P2_(1/c) (No. 14),a=7.43280(10) Å, b=8.59740(10) Å, c=27.5143(3) Å, b=96.6990(10°),a=g=900, V=1746.24(4) Å³, T=300(2) K, Z=4, Z′=1, m(Cu K_(α))=0.801 mm⁻¹,32845 reflections measured, 3622 unique (R_(int)=0.0333) which were usedin all calculations. The final wR₂ was 0.1071 (all data) and R_(I) was0.0409 (I≥2 s(I)).

One molecule of Tabernanthalog and one molecule of fumaric acid werepresent in the unit cell. The hydrogen bonding network is shown (FIG.288 ), thus, fumaric acid adopted a 1,4-orientated linear configuration,exhibiting head to tail hydrogen bonding between oxygen atoms O3----O4(2.48 Å), while oxygen atom O2 was hydrogen bonded to nitrogen atom N₁,located on the azepine ring (O02----N1, 2.70 Å), assumed to be salified.

Form A (Pattern #6a) is now definitely characterized. Cameron et al.(Nature, 2021 Jan; 589(7842):474-479) did not contain a crystallographicinformation file and a search of the Cambridge Crystallographic Database, did not reveal a hit set for Tabernanthalog or its salts, onlyoriginator Ibogaine. Accordingly, this phase is a novel and stablepolymorph.

The simulated powder pattern obtained from the single crystaldiffraction data at 300° K, adequately explained the experimentallyobserved powder diffraction pattern of Form A (11-M2 (ExperimentReference 11-Sample Reference M2)), at the same temperature.

Comparison of simulated powder pattern (11-M2 (Experiment Reference11-Sample Reference M2)) and experimentally obtained powder diffractionpattern for 6-S2 (Experiment Reference 6-Sample Reference S2) (Form A,Pattern #6a, reference) is provided in FIG. 289 . XRPD diffractogramoverlay of simulated powder diffraction pattern of (11-M2 (ExperimentReference 11-Sample Reference M2); Form A) and 6-S2 ((ExperimentReference 6-Sample Reference S2), red, Form A reference) is provided inFIG. 289A.

Void space was calculated for solvent accessible surface (FIG. 290 ).For illustration, the void space was arbitrarily calculated for minimumprobe radii of 0.6 and 0.9 Å (for example, well beneath that of water at1.4 Å). No regular voids in the crystal structure were large enough toaccommodate non-crystal-bonded, molecular water.

(ii) SCXRD Form I (Pattern #14)

The crystalline tabernanthalog hemifumarate (Pattern #14) ischaracterized by XRPD signals as forth in Table 123.

Crystal Data for 11-Q2 (Experiment Reference 11-Sample Reference Q2)(Form I, refer to FIG. 291 ). C_(8.12)H_(10.5)NO_(1.62), M_(r)=148.17,monoclinic, C₂/c (No. 15), a=21.7386(8) Å, b=9.7033(5) Å, c=15.8640(8)Å, b=99.182(4)°, a=g=900, V=3303.4(3) Å³, T=300(2) K, Z=16, Z′=2, m(CuK_(α))=0.680 mm⁻¹, 11278 reflections measured, 3227 unique(R_(int)=0.0472) which were used in all calculations. The final wR₂ was0.2751 (all data) and R_(I) was 0.0857 (I≥2 s(I)).

One molecule of Tabernanthalog and one-half molecule of fumaric acidwere present in the unit cell; in addition, non-crystal bonded methanol(disordered) was present in a structural pocket.

The hydrogen bonding network is shown; thus, fumaric acid was situatedin-between two molecules of Tabernanthalog via hydrogen bonds to theazepine (N1----O2, 2.70 Å) and indole nitrogen atoms (N2----O3, 2.81 Å).The methanol molecule is not crystal-bonded to the API, i.e., it islocated in a structural pocket and will tumble, within this pocket,contributing to its disorder; this mode of solvent occupancy would beclassified as a channel, or non-stoichiometric solvate. Because theprecise location of the methanol within the pocket is not known, due tonon-crystal bonding and tumbling, there is uncertainty regarding thestoichiometry; however, methanol is estimated to be 0.25 moleculeoccupancy in the unit cell. Expungement of methanol from the crystal atlow pressure and/or relative humidity, is expected to be facile andshould not result in major re-organization of the crystal structure.Form I, hemi-fumarate is definitively characterized. Hydrogen bondingnetwork of Tabernanthalog hemifumarate (Pattern #14, Form I) is providedin FIG. 292 .

The simulated powder pattern obtained from the single crystaldiffraction data at 300° K (11-Q2 (Experiment Reference 11-SampleReference Q2)), explained the experimentally observed powder diffractionpattern at the same temperature, of previously assigned Form I (Pattern#14), tabernanthalog hemifumarate (reference 5-B3 (Experiment Reference5-Sample Reference B3), FIG. 293 ).

XRPD diffractogram overlay of simulated powder diffraction pattern(11-Q2 (Experiment Reference 11-Sample Reference Q2), Form I) and 5-B3((Experiment Reference 5-Sample Reference B3), Form I reference) isprovided in FIG. 293A.

Unit cell volume of tabernanthalog hemifumarate, Pattern #14, Form I(3303 Å) was almost double that of the tabernanthalog monofumarate salt,Pattern #6a, Form A (1746 Å), consistent with greater vacancy in thestructure (FIG. 294 ). The pocket in which the methanol molecule residesis shown (refer to green atom label O4 and the methanol moleculeappeared to be ‘doubled-up’, because of uncertainty regarding itsposition due to tumbling, i.e. contributed to disordering). Void spacewas calculated for solvent accessible surface and contingent on localsolvent activities, it may be possible to exchange the methanol moleculeby small molecules such as water, acetone etc.

E. Characterisation Data

The Tabernanthalog Monofumarate Salt (Sample Reference 1, Pattern #1)

IUPAC name is 8-methoxy-3-methyl-1H,2H,3H,4H,5H,6H-azepino[4,5-b]indolefumarate [Mass: 346.383; Exact mass: 346.152871816; Formula: C₁₈H2₂N₂O₅;and Composition: C (62.42%), H (6.40%), N (8.09%), O (23.09%)].

Table 154 lists a summary of the characterization data of the batch usedto for the polymorph screen experiments.

TABLE 154 Batch used to for the polymorph screen experiments MeCN KFtitre Batch HPLC Q ¹H NMR content (% w/w XRPD reference (% area) (% w/w)(% w/w) water) assignment Sample 97.64 93.13 0.16 2.6* Pattern #1Reference 1 *Theoretical hemihydrate = 2.5% w/w, 355.4 molg⁻¹

¹H NMR spectra are provided in FIGS. 295 and 296 . XRPD results areprovided in FIGS. 297 and 298 and Tables 155 and 156.

TABLE 155 Peak angle data of the tabernanthalog monofumarate salt(Pattern #1, Sample Reference 1) 2-θ (°) d Value Rel. Intensity (%) 9.09.77 21 14.2 6.23 11 16.3 5.43 70 16.7 5.31 28 17.4 5.08 13 17.7 5.01 1018.1 4.90 26 19.3 4.60 43 22.3 3.98 19 23.1 3.85 12 25.1 3.54 16 25.53.49 100 26.1 3.41 13 26.8 3.33 23 27.2 3.27 23 30.0 2.98 11

TABLE 156 Peak angle data of the tabernanthalog monofumarate salt ground(Pattern #1, Sample Reference 1) 2-θ (°) d Value Rel. Intensity (%) 9.09.79 20 15.6 5.67 14 16.3 5.43 69 16.7 5.29 28 17.4 5.08 15 17.8 4.99 1418.1 4.90 23 18.8 4.72 11 19.3 4.59 37 22.3 3.98 18 23.1 3.84 11 24.63.62 17 25.1 3.54 11 25.5 3.48 100 26.2 3.40 11 26.8 3.32 22 27.2 3.2718

The TGA profile of the tabernanthalog fumarate salt (Sample Reference 1)was acquired at a ramp rate of +10° C./minute (FIG. 299 ). The first TGevent (−2.1% w/w) was consistent with the release of volatiles,potentially water and solvent (water −2.6% w/w+acetonitrile−0.2% w/w).Significant weight loss was observed at higher temperature (>200° C.),attributed to chemical degradation and ablation of the sample.

The DSC profile of the tabernanthalog fumarate salt (Sample Reference 1)was acquired at a ramp rate of +10° C./minute (FIG. 300 ). The DSCprofile exhibited a bimodal transition that corresponds to the meltingof two different crystal forms.

The DVS profiles of the tabernanthalog fumarate salt (SampleReference 1) is provided in FIG. 301 and the PLM data is provided inFIGS. 302 and 303 . The SEM data is provided in FIGS. 304-307 . As canbe seen in FIG. 307 (resolution at 2500×), large irregular particleswere observed. SEM surface topography appeared to consist of tightlycompacted foliated plates. Bright particles at wide field wereassociated with electrical discharge effects. HPLC profile is providedin FIG. 308 .

Summary of Forms

i. Monofumarate Salts

1 Pattern #1 (7-N2, example 2) (Experiment Reference 7-Sample ReferenceN2) The list of representative experiments that resulted in Pattern #1is provided in Table

TABLE 156A List of representative experiments that resulted in Pattern#1. PATTERN #1 1-S1; shifted +0.2° 2θ 6-B1 1-R1; shifted +0.2° 2θ 6-B22-A1 (t = 3 h) 6-C2 2-A2 (t = 24 h); shifted +0.1° 2θ 6-C1 (strained)2-A3 (t = 4 d); shifted +0.1° 2θ 1-E1 (20.6°, 21.9°, 24.6° 2θ) 7-G2 2-A5(t = 14 d) 7-D2 2-A6 (t = 21 d) 6-N2 2-B1 (t = 3 h); shifted +0.1° 2θ6-M2 2-B2 (t = 24 h) 6-M1 2-B3 7-E2 2-B5 1-D1 2-B6 6-O1 6-I1 7-N2 6-I21-T1 7-C1 1-O1 7-C2 7-R1 7-I1; shifted +0.1° 2θ 7-I2 9-B1 7-L2 15-T0(CAT8931) 2-B4; shifted +0.1° 2θ 9-B2 2-A4; shifted +0.1° 2θ 11-G2

Preparation

Pattern #1 was prepared in acetonitrile/water or in 2Me-THF.

The characterization data of 7-N2 (Experiment Reference 7-SampleReference N2) is provided in FIG. 4 , FIG. 309 , FIG. 311 , and FIG. 312and Table 157.

TABLE 157 Peak angle data of 7-N2 (Experiment Reference 7-SampleReference N2) (oven dried) 2-θ (°) d Value Rel. Intensity (%) 5.1 17.4131 6.7 13.15 11 9.0 9.78 24 10.2 8.69 29 16.3 5.43 70 16.7 5.30 33 17.45.09 16 17.7 5.00 13 18.1 4.90 26 19.3 4.60 43 22.3 3.99 22 23.0 3.86 1225.2 3.54 18 25.5 3.49 100 26.1 3.41 14 26.8 3.32 23 27.2 3.27 27 29.92.98 12

2. Pattern #2a (Form B, unary fumarate, 7-B2 (Experiment Reference7-Sample Reference 1B2)) The list of representative experiments thatresulted in Pattern #2a is provided in Table 157A.

TABLE 157A List of representative experiments that resulted in Pattern#2a. PATTERN #2a   7-J1 7-J2 7-M1 7-B1 (v. br., high background) 7-B27-O2 (little strained) 1-B1 7-M2

Preparation

Pattern #2a was prepared in acetonitrile.

The characterization data of 7-B2 (Experiment Reference 7-SampleReference B2) is provided in FIG. 3 , FIG. 313 , FIG. 315 and FIG. 316and Table 158.

TABLE 158 XRPD Signal angle data of 7-B2 (Experiment Reference 7-SampleReference B2) (oven dried) 2-θ d Rel. (°) Value Intensity (%)  9.1 9.7331 12.3 7.20 22 14.2 6.21 15 15.7 5.64 28 16.4 5.42 86 17.1 5.18 62 17.45.09 13 18.1 4.90 24 18.8 4.71 11 20.7 4.29 24 21.0 4.22 16 22.3 3.98 1122.8 3.90 19 23.0 3.87 31 24.7 3.60 13 25.0 3.55 21 25.6 3.48 100 26.83.32 28 27.3 3.26 29

3. Pattern #2b (6-G2 (Experiment Reference 6-Sample Reference G2))

The list of representative experiments that resulted in Pattern #2b isprovided in Table

TABLE 158A List of representative experiments that resulted in Pattern#2b PATTERN #2b 6-H2 6-A2 6-Q2 6-G2 6-L2 7-H2

Preparation

Pattern #2b was prepared in ethyl acetate.

The characterization data of 6-G2 (Experiment Reference 6-SampleReference G2) is provided in FIG. 8 , FIG. 317 , FIG. 319 and FIG. 320and Table 159.

TABLE 159 XRPD Signal angle data of 6-G2-(Experiment Reference 6-SampleReference G2) (oven dried) 2-θ d Rel. (°) Value Intensity (%)  9.0 9.7626 14.2 6.23 13 15.5 5.70 21 15.8 5.59 25 16.3 5.43 80 17.0 5.21 20 17.45.10 17 18.1 4.90 30 18.8 4.72 13 19.4 4.57 17 21.0 4.24 10 22.3 3.98 1622.6 3.94 18 24.6 3.61 39 25.1 3.54 26 25.5 3.48 100 26.8 3.33 23

4. Pattern #2c (1-P2 (Experiment Reference 1-Sample Reference P2))

The list of representative experiments that resulted in Pattern #2c isprovided in Table 159A.

TABLE 159A List of representative experiments that resulted in Pattern#2c. PATTERN #2c 1-P2 1-P1 1-L1 9-A2 9-G1 9-G2 9-E1 9-E2 9-F1 9-F2

Preparation

Pattern #2c was prepared in water.

The characterization data of 1-P2 (Experiment Reference 1-SampleReference P2) is provided in FIGS. 321-325 and Table 160.

TABLE 160 XRPD Signal angle data of 1-P2 (Experiment Reference 1-SampleReference P2) (oven dried) 2-θ d Rel. (°) Value Intensity (%)  9.0 9.8020 16.3 5.44 64 16.7 5.30 34 17.4 5.09 12 17.7 5.00 15 18.1 4.90 19 19.34.60 49 20.2 4.40 10 21.2 4.18 11 22.3 3.99 25 23.0 3.86 13 25.1 3.54 1325.5 3.49 100 26.1 3.41 14 26.8 3.33 17 27.2 3.27 20

5. Pattern #2d (7-H1 (Experiment Reference 7-Sample Reference H1))

The list of representative experiments that resulted in Pattern #2d isprovided in Table 160A.

TABLE 160A List of representative experiments that resulted in Pattern#2d. PATTERN #2d 7-H1 6-H1

Preparation

Pattern #2d was prepared in ethyl formate.

XRPD data of 7-H1 (Experiment Reference 7-Sample Reference H1) isprovided in FIG. 326 and Table 161. 7-H1(Experiment Reference 7-SampleReference H1) converted to Pattern #2b upon oven-drying (7-H2)(Experiment Reference 7-Sample Reference H2).

TABLE 161 XRPD Signal angle data of 7-H1 (Experiment Reference 7-SampleReference H1) (wet pellet). 2-θ d Rel. (°) Value Intensity (%)  9.1 9.7229 14.2 6.21 15 16.2 5.46 57 16.3 5.43 81 17.5 5.05 15 18.1 4.90 21 19.94.46 17 21.1 4.20 17 22.1 4.02 28 25.2 3.54 37 25.6 3.48 100 26.0 3.4327 26.8 3.32 25 27.2 3.28 11 28.6 3.12 10 30.0 2.98 11

6. Pattern #3 (6-R2 (Experiment Reference 6-Sample Reference R2))

The list of representative experiments that resulted in Pattern #3 isprovided in Table

TABLE 161A List of representative experiments that resulted in Pattern#3. PATTERN #3 6-D2 6-D1 6-R1 (disordered) 6-R2 7-D1 9-D1 9-D2

Preparation

Pattern #3 was prepared in toluene.

The characterization data of 6-R2 (Experiment Reference 6-SampleReference R2) is provided in FIG. 12 , FIG. 327 , FIG. 329 and FIG. 330and Table 162.

TABLE 162 XRPD Signal angle data of 6-R2 (Experiment Reference 6-SampleReference R2) (oven dried) 2-θ d Rel. (°) Value Intensity (%)  8.4 10.5113.2011  9.0 9.78 24.8928  9.8 9.06 5.6975 11.1 7.94 18.5193 12.5 7.1015.6155 14.3 6.20 14.1395 14.4 6.15 15.5720 16.3 5.43 82.2143 16.6 5.3464.8774 16.8 5.26 28.3532 17.4 5.09 11.0713 18.0 4.91 21.7920 18.8 4.7327.8544 19.3 4.59 12.9813 20.1 4.41 40.6675 22.2 4.00 37.7836 22.5 3.9423.1797 24.7 3.60 16.5107 25.0 3.55 19.1800 25.5 3.49 100.0000 26.0 3.4239.9175 26.8 3.33 28.4983 27.2 3.27 11.0895 29.9 2.98 10.9865

7. Pattern #4a (6-K2 (Experiment Reference 6-Sample Reference K2))

The list of representative experiments that resulted in Pattern #4a isprovided in Table 162A.

TABLE 162A List of representative experiments that resulted in Pattern#4a. PATTERN #4a 6-P2 6-F2 6-K1 6-K2

Preparation

Pattern #4a was prepared in methanol.

The characterization data of 6-K2 (Experiment Reference 6-SampleReference K2) is provided in FIG. 10 , FIG. 331 , FIG. 333 and FIG. 334and Table 163.

TABLE 163 XRPD Signal angle data of 6-K2 (Experiment Reference 6-SampleReference K2) (oven dried) 2-θ d Rel. (°) Value Intensity (%)  8.2 10.7952  9.0 9.78 27 11.3 7.85 31 12.7 6.95 12 14.2 6.23 14 15.6 5.67 17 16.35.43 89 17.1 5.18 25 18.0 4.91 22 18.9 4.69 16 19.3 4.60 25 19.4 4.57 2420.4 4.35 18 20.5 4.32 21 21.5 4.13 23 22.6 3.93 16 23.8 3.74 26 25.23.53 17 25.5 3.49 100 26.8 3.33 24 30.0 2.98 10

9. Pattern #4b (6-O2 (Experiment Reference 6-Sample Reference O2))

The list of representative experiments that resulted in Pattern #4b isprovided in Table 163A.

TABLE 163A List of representative experiments that resulted in Pattern#4b. PATTERN #4b 6-E2 6-E1 6-O2

Preparation

Pattern #4b was prepared in nitromethane.

The characterization data of 6-O2 (Experiment Reference 6-SampleReference O2) is provided in FIG. 11 , FIG. 335 , FIG. 337 and FIG. 338and Table 164.

TABLE 164 XRPD Signal angle data of 6-O2 (Experiment Reference 6-SampleReference O2) (oven dried) 2-θ d Rel. (°) Value Intensity (%)  8.2 10.7125  9.1 9.76 25 11.3 7.86 16 14.2 6.22 12 15.7 5.66 19 16.3 5.43 84 16.85.27 11 17.2 5.15 23 17.4 5.10 13 18.1 4.90 23 18.8 4.71 10 19.3 4.60 1320.4 4.35 14 21.4 4.14 13 21.5 4.12 17 22.4 3.97 10 22.6 3.93 16 23.93.73 15 25.2 3.54 14 25.6 3.48 100 26.8 3.32 22 27.3 3.27 17

9. Pattern #6a (Form A, unary fumarate, 6-S2 (Experiment Reference6-Sample Reference S2))

The list of representative experiments that resulted in Pattern #6a isprovided in Table 164A.

TABLE 164A List of representative experiments that resulted in Pattern#6a. PATTERN #6a 6-S2 (strain) 11-O2 6-S1 11-N2 11-A2 8-A1 11-B2 8-A211-F2 8-A3 11-H2 8-A4 11-J2 14-C1 11-L2 14-C2 11-M2 * Strain refers tochange across unit cell axis and leads to change in d-spacing thatcauses small shift in peak angle reflection (ca. 0.1 to 0.3° 2-θ).

Preparation

Pattern #6a was prepared in water.

The characterization data of 6-S2 (Experiment Reference 6-SampleReference S2) is provided in FIG. 13 , FIG. 344 , FIG. 345 , FIG. 347and FIG. 348 and Table 166 and Table 166-A. DVS analyses of Form A isprovided in FIG. 78 .

TABLE 166 XRPD Signal angle data of 6-S2 (Experiment Reference 6-SampleReference S2) (oven dried) 2-θ d Rel. (°) Value Intensity (%) 13.0 6.7911 16.6 5.33 78 19.3 4.59 38 19.6 4.52 100 20.7 4.29 68 22.1 4.01 2225.4 3.50 63 26.2 3.40 34 33.6 2.67 12

TABLE 166A Peak table of a calculated powder pattern for tabernanthalogmonofumarate, Pattern #6a, Form A. Peak Rel number 2-θ (°) Intensity %Peak #1 12.9 10 Peak #2 16.6 100 Peak #3 18.7 10 Peak #4 19.3 25 Peak #519.6 95 Peak #6 20.6 94 Peak #7 22.1 22 Peak #8 25.3 90 Peak #9 26.1 31Peak #10 26.3 11 Peak #11 33.5 14 Peak #12 37.8 12

10. Pattern #6b (Form A, 1-K2 (Experiment Reference 1-Sample ReferenceK2))

The list of representative experiments that resulted in Pattern #6b isprovided in Table 166B.

TABLE 166B List of representative experiments that resulted in Pattern#6b. PATTERN #6b 1-K2 1-K1 11-E2 11-I2

Preparation

Pattern #6b was prepared in methanol.

The characterization data of 1-K2 (Experiment Reference 1-SampleReference K2) is provided in FIGS. 349-353 and Table 167.

TABLE 167 XRPD Signal angle data of 1-K2 (Experiment Reference 1-SampleReference K2) (oven dried) 2-θ d Rel. (°) Value Intensity (%)  8.2 10.7212 12.9 6.84 14 16.5 5.37 79 19.4 4.56 100 20.5 4.32 72 22.0 4.04 1625.3 3.52 44 26.0 3.42 37 33.4 2.68 12 37.7 2.38 11

11. Pattern #7 (6-N1) (Experiment Reference 6-Sample Reference N1) Thelist of representative experiments that resulted in Pattern #7 isprovided in Table 167A.

TABLE 167A List of representative experiments that resulted in Pattern#7. PATTERN #7 6-N1 1-M1 7-N1

Preparation

Pattern #7 was prepared in 2-MeTHF.

The characterization data of (6-N1) (Experiment Reference 6-SampleReference N1) is provided in FIG. 354 and Table 168. It is worth notingthat 7-N1 (Experiment Reference 7-Sample Reference N1) converted toPattern #2b upon oven-drying (7-N2) (Experiment Reference 7-SampleReference N2).

TABLE 168 XRPD Signal angle data of 6-N1 (wet pellet) (ExperimentReference 6-Sample Reference N1) 2-θ d Rel. (°) Value Intensity (%)  7.212.25 36  9.1 9.71 26 14.3 6.20 15 15.9 5.56 59 16.4 5.42 100 16.8 5.2723 17.5 5.06 11 18.2 4.88 20 19.4 4.58 28 19.8 4.48 25 20.8 4.26 13 21.34.17 25 22.5 3.95 20 24.9 3.57 34 25.6 3.48 99 26.9 3.32 20 27.3 3.27 22

12. Pattern #8 (6-J2) (Experiment Reference 6-Sample Reference J2) Thelist of representative experiments that resulted in Pattern #8 isprovided in Table 168A.

TABLE 168A List of representative experiments that resulted in Pattern#8. PATTERN #8 6-J1 6-J2 1-J1 7-S1 (Predom. amorph.) 9-C1 9-C2

Preparation

Pattern #8 was prepared in isopropyl acetate.

The characterization data of (6-J2) (Experiment Reference 6-SampleReference J2) is provided in FIG. 9 , FIG. 355 , FIG. 357 , and FIG. 358and Table 169.

TABLE 169 XRPD Signal angle data of 6-J2 (oven dried) (ExperimentReference 6-Sample Reference J2) 2-θ d Rel. (°) Value Intensity (%)  7.611.69 23  9.0 9.79 23 14.2 6.24 11 15.8 5.59 64 16.3 5.44 90 17.4 5.1014 18.0 4.92 24 18.9 4.70 14 19.0 4.66 23 19.5 4.55 11 20.5 4.32 37 21.94.05 11 22.3 3.99 11 22.5 3.94 15 24.2 3.67 60 24.8 3.59 26 25.5 3.49100 26.7 3.33 20 27.2 3.28 15

13. Pattern #9 (6-G1) (Experiment Reference 6-Sample Reference G1)

The list of representative experiments that resulted in Pattern #9 isprovided in Table 169A.

TABLE 169A List of representative experiments that resulted in Pattern#9. PATTERN #9 6-G1 1-H1 7-G1

Preparation

Pattern #9 was prepared in ethyl acetate.

The characterization data of 6-G1 is provided in FIG. 359 and Table 170.It is noted that 7-G1 (Experiment Reference 7-Sample Reference G1)converted to Pattern #2b upon oven-drying 7-G2 (Experiment Reference7-Sample Reference G2).

TABLE 170 XRPD Signal angle data of 6-G1 (wet pellet) (ExperimentReference 6-Sample Reference G1) 2-θ d Rel. (°) Value Intensity (%)  8.011.05 32  9.2 9.63 27 10.5 8.43 13 12.2 7.27 13 14.3 6.17 14 15.9 5.56100 16.4 5.39 78 17.1 5.18 35 18.2 4.87 18 19.2 4.63 15 19.5 4.56 4120.8 4.27 25 21.9 4.06 39 22.4 3.96 15 24.7 3.60 84 25.6 3.47 96 27.03.30 21 27.3 3.27 10 28.8 3.09 18

14. Pattern #10 (6-P1) (Experiment Reference 6-Sample Reference P1)

The list of representative experiments that resulted in Pattern #10 isprovided in Table 170A.

TABLE 170A List of representative experiments that resulted in Pattern#10. PATTERN #10 6-P1 1-I1 7-P1

Preparation

Pattern #10 was prepared in 2-propanol.

The characterization data of 6-P1 is provided in FIG. 360 and Table 171.It is noted that 7-P1 (Experiment Reference 7-Sample Reference P1)converted to Pattern #4a upon oven-drying (7-P2) (Experiment Reference7-Sample Reference P2).

TABLE 171 XRPD Signal angle data of 6-P1 (wet pellet) (ExperimentReference 6-Sample Reference P1) 2-θ d Rel. (°) Value Intensity (%)  8.210.78 47  9.1 9.75 41 10.8 8.17 42 14.2 6.21 20 15.2 5.82 37 16.3 5.4394 16.9 5.25 96 17.4 5.08 12 18.0 4.91 23 18.8 4.71 12 19.1 4.63 17 19.64.51 21 19.8 4.48 39 21.3 4.16 56 21.8 4.07 29 22.2 4.00 27 22.6 3.94 1523.4 3.80 41 23.5 3.79 53 23.6 3.76 32 25.2 3.53 22 25.5 3.48 100 26.13.41 12 26.8 3.33 31 29.8 3.00 15

15. Pattern #11 (6-Q1) (Experiment Reference 6-Sample Reference Q1)

The list of representative experiments that resulted in Pattern #11 isprovided in Table 171 Å.

TABLE 171A List of representative experiments that resulted in Pattern#11. PATTERN #11 6-Q1 1-N1 7-Q1

Preparation

Pattern #11 was prepared in THF.

The characterization data of 6-Q1 is provided in FIG. 361 and Table 172.

TABLE 172 XRPD Signal angle data of 6-Q1 (wet pellet) (ExperimentReference 6-Sample Reference Q1) 2-θ d Rel. (°) Value Intensity (%)  7.511.76 39  9.2 9.64 27 10.8 8.22 14 11.2 7.88 16 14.3 6.17 11 16.1 5.49100 16.4 5.40 66 17.4 5.09 22 18.2 4.87 15 20.4 4.36 51 20.9 4.25 2221.6 4.11 59 22.5 3.94 13 22.8 3.90 19 23.9 3.72 24 24.0 3.70 16 25.33.52 14 25.7 3.46 80 27.0 3.30 16

16. Pattern #12 (6-A1) (Experiment Reference 6-Sample Reference A1)

The list of representative experiments that resulted in Pattern #12 isprovided in Table 172A.

TABLE 172A List of representative experiments that resulted in Pattern#12 PATTERN #12 6-A1 1-A1

Preparation

Pattern #12 was prepared in acetone.

The characterization data of 6-A1 is provided in FIG. 362 and Table 173.It is noted that 7-A1 (Experiment Reference 7-Sample Reference A1)converted to Pattern #2b upon oven-drying (7-A2) (Experiment Reference7-Sample Reference A2).

TABLE 173 XRPD Signal angle data of (6-A1) (wet pellet) (ExperimentReference 6-Sample Reference A1) 2-θ d Rel. (°) Value Intensity (%)  8.310.64 25  9.1 9.67 24 10.8 8.17 14 14.3 6.18 14 16.3 5.42 100 18.2 4.8621 20.3 4.37 26 21.6 4.11 30 23.0 3.87 18 25.6 3.47 96

17. Pattern #13 (7-L1) (Experiment Reference 7-Sample Reference L1)

The list of representative experiments that resulted in Pattern #13 isprovided in Table 173A.

TABLE 173A List of representative experiments that resulted in Pattern#13. PATTERN #13 7-L1 6-L1

Preparation

Pattern #13 was prepared in methyl acetate.

The characterization data of 7-L1 is provided in FIG. 363 and Table 174.

TABLE 174 XRPD Signal angle data of 7-L1 (wet pellet) (ExperimentReference 7-Sample Reference L1) 2-θ (°) d Value Rel. Intensity (%) 8.110.91 28 18. 1 4.89 18 18.9 4.69 10 19.7 4.50 42 20.9 4.24 19 21.9 4.0527 22.7 3.91 16 23.4 3.81 12 24.5 3.64 12 25.0 3.56 59 25.6 3.47 100 9.19.68 23 26.9 3.31 19 28.7 3.11 12 10.5 8.41 19 14.3 6.19 11 16.0 5.53 7816.4 5.41 75 17.5 5.07 37

18. Pattern #15 ((1-C2) (Experiment Reference 1-Sample Reference C2))

The list of representative experiments that resulted in Pattern #15 isprovided in Table 174A.

TABLE 174A List of representative experiments that resulted in Pattern#15. PATTERN #15 1-C2 1-C1

Preparation

Pattern #15 was prepared in butanol.

The characterization data of 1-C2 is provided in FIG. 1 , FIG. 368 ,FIG. 370 , FIG. 371 and FIG. 372 and Table 176.

TABLE 176 XRPD Signal angle data of 1-C2 (oven dried) (ExperimentReference 1-Sample Reference C2) 2-θ (°) d Value Rel. Intensity (%) 8.410.51 24.0824 9.0 9.84 17.0488 10.5 8.39 16.7679 15.0 5.90 18.8008 16.25.46 100.0000 16.9 5.24 33.2111 17.0 5.21 66.3567 17.7 5.01 17.5463 18.04.92 19.8925 18.9 4.70 14.2790 19.2 4.61 10.7662 19.9 4.46 30.8267 21.04.22 46.5241 22.5 3.96 12.6072 23.3 3.82 49.3726 23.6 3.77 13.7509 24.43.64 25.9068 24.8 3.58 12.4289 25.1 3.54 21.2087 25.5 3.49 61.0403 26.03.42 18.0249 26.7 3.33 13.4083

19. Pattern #16 (1-F1) (Experiment Reference 1-Sample Reference F1) Thelist of representative experiments that resulted in Pattern #16 isprovided in Table 176A.

TABLE 176A List of representative experiments that resulted in Pattern#16. PATTERN #16 1-F1

Preparation

Pattern #16 was prepared in diethyl ether.

The characterization data of 1-F1 is provided in FIG. 373 and Table 177.

TABLE 177 XRPD Signal angle data of 1-F1 (wet pellet) (ExperimentReference 1-Sample Reference F1) 2-θ (°) d Value Rel. Intensity (%) 9.09.81 13 9.1 9.75 25 9.6 9.18 24 14.2 6.21 12 16.4 5.42 76 16.8 5.27 2517.0 5.21 38 17.5 5.06 13 17.8 4.99 19 18.1 4.89 23 19.0 4.66 14 19.34.59 35 20.3 4.38 15 22.4 3.97 20 23.2 3.84 11 23.8 3.73 12 24.4 3.65 3625.2 3.53 15 25.6 3.48 100 26.2 3.40 12 26.8 3.32 17 27.3 3.27 19

20. Pattern #17 (7-O1) (Experiment Reference 7-Sample Reference O1) Thelist of representative experiments that resulted in Pattern #17 isprovided in Table 177A.

TABLE 177A List of representative experiments that resulted in Pattern#17. PATTERN #17 7-01

Preparation

Pattern #17 was prepared in nitromethane.

The characterization data of 7-O1 is provided in FIG. 374 and Table 178.

TABLE 178 XRPD Signal angle data of 7-01 (wet pellet) (ExperimentReference 7-Sample Reference 01) 2-θ (°) d Value Rel. Intensity (%) 8.110.87 18 9.1 9.69 27 11.2 7.89 18 14.3 6.19 12 15.4 5.76 17 16.4 5.39 8516.6 5.33 78 18.1 4.89 21 19.6 4.52 42 21.2 4.18 11 21.7 4.08 45 22.43.96 26 23.2 3.83 26 23.6 3.77 56 25.2 3.53 17 25.6 3.47 100 26.9 3.3138 27.1 3.28 20 30.3 2.95 13

21. Pattern #18 (Sample Reference 1, cold cryst., 150° C.)

The list of representative experiments that resulted in Pattern #18 isprovided in Table 178A.

TABLE 178A List of representative experiments that resulted in Pattern#18. PATTERN #18 Tabernanthalog monofumarate, Sample Reference 1, coldcryst., 150° C.

Preparation N/A

The characterization data of Sample Reference 1 is provided in FIG. 375and Table 179.

TABLE 179 XRPD Signal angle data of tabernanthalog DSC XRPD 150C (SampleReference 1), cold cryst., 150° C. 2-θ (°) d Value Rel. Intensity (%)8.7 10.19 11 9.1 9.72 12 11.0 8.00 23 12.1 7.28 12 12.6 7.03 15 14.16.28 17 15.5 5.70 25 16.0 5.52 96 16.3 5.45 45 16.8 5.29 14 18.0 4.93 8618.9 4.69 20 19.3 4.60 16 20.9 4.24 19 21.4 4.15 35 22.4 3.96 17 23.03.87 29 24.9 3.58 12 25.6 3.47 100 25.9 3.43 27 26.8 3.33 30

22. Pattern #19 (7-A1; Experiment Reference 7-Sample Reference A1) Thelist of representative experiments that resulted in Pattern #19 isprovided in Table 179A.

TABLE 179A List of representative experiments that resulted in Pattern#19. PATTERN #19 7-A1 7-A2

Preparation

Pattern #19 was prepared in acetone.

The characterization data of 7-A1 is provided in FIG. 376 and Table 180.

TABLE 180 XRPD Signal angle data of 7-A1 (wet pellet) (ExperimentReference 7-Sample Reference A1) 2-θ (°) d Value Rel. Intensity (%) 9.19.74 18 12.2 7.27 11 15.7 5.66 12 16.3 5.43 55 16.4 5.41 78 17.0 5.21 2418.6 4.77 13 19.4 4.58 25 19.5 4.54 27 20.5 4.33 73 21.5 4.13 17 21.94.05 16 22.8 3.90 30 24.7 3.60 14 25.5 3.49 90 25.6 3.48 100 26.7 3.3431 27.1 3.28 17 29.8 2.99 11 33.3 2.69 18

23. Pattern #20 (1-Q1; Experiment Reference 1-Sample Reference Q1)

The list of representative experiments that resulted in Pattern #20 isprovided in Table 180A.

TABLE 180A List of representative experiments that resulted in Pattern#20. PATTERN #20 1-Q1

Preparation

Pattern #20 was prepared in 1,4-dioxane.

The characterization data of 1-Q1 is provided in FIG. 377 and Table 181.

TABLE 181 XRPD Signal angle data of 1-Q1 (wet pellet; Pattern #20) 2-θ(°) d Value Rel. Intensity (%) 6.1 14.54 100 15.9 5.57 13 16.3 5.43 2716.7 5.32 12 18.2 4.87 25 19.0 4.66 27 25.5 3.49 37

ii. Hemifumarate Salts

1. Pattern #5 (1-G2 (Experiment Reference 1-Sample Reference G2)) Thelist of representative experiments that resulted in Pattern #5 isprovided in Table 181A.

TABLE 181A List of representative experiments that resulted in Pattern#5. PATTERN #5 1-G2 1-G1 7-F1 6-F1 11-P2 11-K2 11-D2

Preparation

Pattern #5 was prepared in ethanol.

The characterization data of 1-G2 (Experiment Reference 1-SampleReference G2) is provided in FIG. 2 , FIGS. 377A-337D and Table 181B. Inthe TGA profile, the weight loss transition (−5.8% w/w) attributed toethanol release (probable ethanol, hemi-solvate).

TABLE 181B XRPD Signal angle data of 1-G2 (Experiment Reference 1-SampleReference G2) (oven dried) 2-θ (°) d Value Rel. Intensity (%) 8.2 10.75100 11.1 7.97 38 12.8 6.94 10 15.4 5.76 37 16.3 5.43 15 16.9 5.23 8219.1 4.64 16 20.0 4.44 42 21.4 4.15 56 22.2 4.00 18 22.5 3.95 31 23.63.77 46 23.9 3.72 28 25.5 3.49 33 26.8 3.32 10 30.2 2.95 21

2. Pattern #14 (Form I, hemi-fumarate, 5-B3) (Experiment Reference5-Sample Reference B3)

The list of representative experiments that resulted in Pattern #14 isprovided in Table 181C.

TABLE 181C List of representative experiments that resulted in Pattern#14. PATTERN #14  5-03 (re-proportionation)  5-02 (re-proportionation) 5-B2  5-B3 11-Q2

Preparation

Pattern #14 was prepared in isopropyl acetate.

The characterization data of 5-B3 (Form I, hemi-fumarate) is provided inFIGS. 377E-377J and Table 181D and Table 181E.

TABLE 181D XRPD Signal angle data of (5-B3) (Experiment Reference5-Sample Reference B3) 2-θ (°) d Value Rel. Intensity (%) 8.2 10.79 10011.2 7.90 36 12.8 6.93 10 15.5 5.70 56 17.0 5.21 54 18.1 4.91 18 18.44.83 13 19.2 4.61 17 19.4 4.56 13 20.2 4.39 44 21.3 4.17 13 21.5 4.13 2922.6 3.93 51 23.7 3.75 32 24.3 3.67 17 24.8 3.59 31

TABLE 181E Peak table of a calculated powder pattern for tabernanthaloghemifumarate, Pattern #14, Form I (11-Q2). 2-θ (°) Rel Intensity % 8.2100 11.3 62 12.9 18 15.4 11 15.6 38 17.1 51 19.1 18 20.3 40 21.2 14 21.545 22.7 14 22.9 11

3. Pattern #21 (7-P2; Experiment Reference 7-Sample Reference P2)

The list of representative experiments that resulted in Pattern #21 isprovided in Table 181F.

TABLE 181F List of representative experiments that resulted in Pattern#21. PATTERN #21 7-P2

Preparation

Pattern #21 was prepared in isopropanol.

The characterization data of 7-P2 is provided in FIG. 5 , FIG. 378 ,FIG. 380 and FIG. 381 and Table 182.

TABLE 182 XRPD Signal angle data of 7-P2 (oven dried) (ExperimentReference 7-Sample Reference P2) 2-θ (º) d Value Rel. Intensity (%) 6.713.15 23 8.2 10.74 11 12.8 6.89 16 14.9 5.94 13 16.3 5.45 10 16.7 5.3180 17.6 5.04 16 17.7 5.01 30 18.1 4.89 31 19.2 4.61 100 20.1 4.41 2321.2 4.19 27 22.2 3.99 38 23.0 3.86 16 23.6 3.77 16 25.4 3.50 55 26.13.41 26 27.2 3.28 36 28.7 3.11 15 30.1 2.96 13

4. Pattern #22 (10-B1; Experiment Reference 10-Sample Reference B1)

The list of representative experiments that resulted in Pattern #22 isprovided in Table 182A.

TABLE 182A List of representative experiments that resulted in Pattern#22. PATTERN #22 10-B1

Preparation

Pattern #22 was prepared in water.

The characterization data of 10-B1 is provided in FIGS. 382-383 andTable 183.

TABLE 183 XRPD Signal angle data of 10-B1 (Experiment Reference10-Sample Reference B1) 2-θ (º) d Value Rel. Intensity (%) 6.7 13.18 2410.4 8.50 14 12.9 6.87 12 15.0 5.90 18 16.7 5.29 48 17.7 4.99 22 18.24.87 32 18.9 4.70 100 19.3 4.59 83 20.2 4.39 21 21.3 4.17 13 22.3 3.9821 23.1 3.84 11 23.7 3.75 15 25.4 3.51 11 25.5 3.49 24 26.2 3.40 19 27.33.27 47

F. Overall Summary

A summary of important findings based on this study is provided below:

-   -   Supplied batch (Sample Reference 1, Pattern #1) exhibited two        potential melt events were evident by DSC (FIG. 300 ).    -   Qualitative solubility:        -   The tabernanthalog monofumarate salt was sparingly soluble            in most of the common solvents investigated and was soluble            in methanol/water (200 mg/ml) at reflux (Experiment            Reference 1)        -   crystallized samples from the qualitative solubility pane,            included those from butanol, ethanol methanol and water,            these were dried and analysed further and supported the            formation of butanol hemi-solvate, ethanol            hemi-fumarate/solvate and anhydrous forms from methanol and            water.    -   Re-proportionation:        -   the hemi-fumarate salt exhibited a propensity to            re-proportionate to the fumarate salt during an ageing cycle    -   Stability evaluation at 40° C./75% RH:        -   executed over a 4 to 5 week period        -   no evidence for hydration was observed    -   Suspension equilibrations:        -   against 20 solvents at two temperature set-points, various            patterns were identified (84)        -   many of these were identified via XRPD analyses of wet            pellets and when dried, often converted into Form A;            therefore, thermal analyses were not possible on the            metastable forms.    -   Single forms identified from the screen included:        -   The tabernanthalog monofumarate salt Form A (Pattern #6a)            was identified as the stable polymorphic form        -   The tabernanthalog monofumarate salt Form B (Pattern #2a),            identified as the metastable polymorphic form        -   Tabernanthalog hemifumarate was also isolated as an enriched            phase and assigned Form I (Pattern #14).        -   Single crystal structures were determined for Form A            (Pattern #6a, 11-M2; Experiment Reference 11-Sample            Reference M2) and Form I (tabernanthalog hemifumarate            (Pattern #14); 11-Q2; Experiment Reference 11-Sample            Reference Q2) (FIGS. 285 and 286 , respectively).        -   Mass equilibrated DVS of Form A (Pattern #6a) was performed            (FIG. 83 and FIG. 84 ). The analysis showed hygroscopic            isotherm with negligible hysteresis.        -   Competitive suspension equilibration studies of equimolar            mixtures of Form A (Pattern #6a) and Form B (Pattern #14) at            temperature set points 20 and 40° C. After stirring at both            temperatures for 4 weeks, Form A (Pattern #6a) was dominant            in the isolated wet pellets indicating that it is more            stable compared to Form B (Pattern #14).

Tables 185-187 summarizes the characterization data of Forms A, B and I,respectively.

TABLE 185 The tabernanthalog Monofumarate salt (Form A, Pattern #6a)Provenances of The tabernanthalog monofumarate salt (Form A, Pattern#6a, reference batches unary fumarate) 8-A4 (Experiment Referencebatches: Reference 8- 6-S1 (Experiment Reference 6-Sample Reference S1),Sample Reference 6-S2 (Experiment Reference 6-Sample Reference S2), A4):obtained from 11-A2 (Experiment Reference 11-Sample Reference A2),suspension 11-B2 (Experiment Reference 11-Sample Reference B2),equilibration of 11-F2 (Experiment Reference 11-Sample Reference F2),tabernanthalog 11-H2 (Experiment Reference 11-Sample Reference H2),monofumarate 11-J2 (Experiment Reference 11-Sample Reference J2),(Sample Reference 11-L2 (Experiment Reference 11-Sample Reference L2),1; Pattern #1) in 11-M2 (Experiment Reference 11-Sample Reference M2),water (5 vol) at 11-N2 (Experiment Reference 11-Sample Reference N2),90° C. The product 11-O2 (Experiment Reference 11-Sample Reference O2),was isolated by 8-A1 (Experiment Reference 8-Sample Reference A1),filtration and dried 8-A2 (Experiment Reference 8-Sample Reference A2),under sustained 8-A3 (Experiment Reference 8-Sample Reference A3),nitrogen flux (<1 8-A4 (Experiment Reference 8-Sample Reference A4),bar) over 20 h at 14-C1 (Experiment Reference 14-Sample Reference C1),and 20° C. 14-C2 (Experiment Reference 14-Sample Reference C2). 6-S2(Experiment Molecular weight: 346.383 gmol⁻¹ Reference 6- Exactmolecular weight: 346.153 Sample Reference Molecular formula: C₁₈H₂₂N₂O₃S2): (obtained from Unary fumarate: 33.5% w/w th., fumaric acid (i.e.,1.0 mol of API to suspension 1.0 mol fumaric acid) equilibration ofNature of hydrogen bonding: fumaric acid adopted a 1,4-orientated SampleReference linear configuration, exhibiting head to tail hydrogen bondingbetween 1 in water (5 vol) oxygen atoms O3—O4 (2.48 Å), while oxygenatom O2 was hydrogen at 20° C. and bonded to nitrogen atom N1, locatedon the azepine ring (O2—N1, isolated as above. 2.70 Å), assumed to besalified. [6-S1 (Experiment Crystal system 300(2): monoclinic (FIG. 285)Reference 6- Space group 300(2): P2₁/c Sample Reference Unit cell 300(2)K: a = 7.43280(10) Å, b = 8.59740(10) Å, c = S1) and 6-S2 27.5143(3) Å,a = g = 90°, b = 96.6990(10)°, V = 1746.24(4) Å³ (Experiment Asymmetricunit: contained one molecule of API and one molecule of Reference 6-fumaric acid (crystal bonded). Sample Reference XRPD: 12.9°, 14.1°,15.8°, 16.5°, 19.2°, 19.4°, 20.6°, 22.0°, 25.2°, 26.0°, S2) gave thesame 28.0°, 33.4°, (2θ, 1 d.p), (8-A4). [Only peaks with >10% rel.intensity powder diffraction are provided.] pattern. The DSC: onset187.0° C. (−117.9 Jg⁻¹, endotherm, melt). thermal data were TGA (onlyablation events): onset 220.8° C. (−16.0% w/w, ablation) collected fromthe 289.5° C. (−1.2% w/w, ablation), 315.3° C. (−1.5% w/w, ablation),dried material.] 325.9° C. (−3.8% w/w, ablation), 373.7° C. (−14.0% w/w,ablation), (8-A4). This is shown in FIG. 148. DVS 0 to 90 to 0% RH(dm/dt <0.002%): 0.0 (0.0004%), 5.0 (0.0627%), 10.0 (0.0957%), 15.0(0.1397%), 20.0 (0.1778%), 25.0 (0.2093%), 30.0 (0.2401%), 40.0(0.3145%), 50.0 (0.4051%), 60.0 (0.5029%), 70.0 (0.5451%), 80.0(0.6660%), 90.0 (0.9766%), 90.0 (0.9766%), 80.0 (0.6827%), 70.0(0.5442%), 60.0 (0.4515%), 50.0 (0.3797%), 40.0 (0.3210%), 30.0(0.2656%), 25.0 (0.2387%), 20.0 (0.2126%), 15.0 (0.1857%), 10.0(0.1551%), 5.0 (0.1179%), 0.0 (0.0381%) (8-A4)as shown in FIG. 78. UVchromatographic purity: 99.04% area (212 nm), (8-A4; ExperimentReference 8-Sample Reference A4 as shown in FIG. 151. 1H NMR: (DMSO-d6,400 MHz); δ 10.6 (s, 1 H), 7.3 (d, J = 8.6 Hz, 1 H), 6.8 (s, 1 H), 6.6(dd, J = 8.6, 2.2 Hz, 1 H), 6.5 (s, 2 H), 3.7 (s, 3 H), 3.1-3.0 (m, 6H), 2.9 (t, J = 9.9, 5.6 Hz, 2 H), 2.6 (s, 3 H) conforms to themolecular structure (Σ[20H*), (8-A4; Experiment Reference 8- SampleReference A4), as shown in FIG. 146. Appearance: refer to FIG. 152 toFIG. 155 of 8-A4; Experiment Reference 8-Sample Reference A4. Solubilityin SIF buffers: Soluble in FaSSIF, FeSSIF and FaSSGF at 37° C. up to 24h. *The molecular formula (C₁₈H₂₂N₂O₅) includes the carboxylic acidprotons; however, they co-resonate with water..

TABLE 186 The tabernanthalog monofumarate salt (Form B, Pattern #2a)Provenances of The tabernanthalog Monofumarate salt (Form B, Pattern#2a, reference batches unary fumarate) 7-B2 (Experiment Referencebatches: Reference 7- 7-J1 (Experiment Reference 7-Sample Reference J1),Sample Reference 7-J2 (Experiment Reference 7-Sample Reference J2), B2):obtained from 7-M1 (Experiment Reference 7-Sample Reference M1),suspension 7-B1 (Experiment Reference 7-Sample Reference B1),equilibration of 7-B2 (Experiment Reference 7-Sample Reference B2),tabernanthalog 7-O2 (Experiment Reference 7-Sample Reference O2),monofumarate 1-B1 (Experiment Reference 1-Sample Reference B1), and(Sample Reference 7-M2 (Experiment Reference 7-Sample Reference M2). 1,Pattern #1) in Molecular weight: 346.383 gmol⁻¹ acetonitrile (5 vol)Exact molecular weight: 346.153 at 40° C. The Molecular formula:C₁₈H₂₂N₂O₅ product was Unary fumarate: 33.5% w/w th., fumaric acid(i.e., 1.0 mol of API to isolated by 1.0 mol fumaric acid).centrifugation and XRPD: 9.1°, 12.3°, 14.2°, 15.7°, 16.4°, 17.1°, 17.4°,18.1°, 18.8°, was oven-dried 20.7°, 21.0°, 22.3°, 22.8°, 23.0°, 24.7°,25.0°, 25.6°, 26.8°, 27.3°, under vacuum over 2θ, 1 d.p), (A1272-022-B2,refer To FIG. 3, [Only peaks with 20 h at 40° C. >10% rel. intensity areprovided.] DSC: onset 100.6° C. (−0.74 Jg⁻¹, endotherm), 125.7 ° C.(−1.57 Jg⁻¹, endotherm) 174.1° C. (−31.27 Jg⁻¹, endotherm, melt); referto FIG. 316. TGA (only ablations events): onset 219.0° C. (−10.3% w/w,ablation) 286.8° C. (−1.9% w/w, ablation), 324.6° C. (−2.5% w/w,ablation); refer to FIG. 315. ¹H NMR: (DMSO-d6, 400 MHz); δ 10.6 (s, 1H), 7.3 (d, J = 8.6 Hz, 1 H), 6.8 (s, 1 H), 6.6 (dd, J = 8.6, 2.2 Hz, 1H), 6.5 (s, 2 H), 3.7 (s,3H), 3.1-3.0 (m, 6 H), 2.9 (t, J =9.9, 5.6 Hz,2 H), 2.6 (s, 3 H) conforms to the molecular structure (Σ20H*) as shownin FIG. 313). Residual solvents ICH Q2C (R8): 7-B2 [acetonitrile (0.1%w/w (0.03% w/w, ICH listed 10 ppm)]. *The molecular formula (C₁₈H₂₂N₂O₅)includes the carboxylic acid protons; however, they co-resonate withwater.

TABLE 187 Tabernanthalog hemifumarate (Form I, Pattern #14) Provenancesof Tabernanthalog hemifumarate (Form I, Pattern #14, hemi- referencebatches fumarate) (5-B3) (Experiment Reference batches: Reference5-Sample 5-03, Reference B3): 5-02, obtained from 5-B2 (ExperimentReference 5-Sample Reference B2) dissolution of 5-B3 (ExperimentReference 5-Sample Reference B3), and tabernanthalog 11-Q2 (ExperimentReference 11-Sample Reference Q2) (native); TBG Native) Molecularweight: 576.694 gmol⁻¹ and fumaric acid (0.5 Exact molecular weight:576.2947 equiv) in methanol (20 Molecular formula: C₃₂H₄₀N₄O₆ vol).Hemi-fumarate: 20.1% w/w th., fumaric acid (i.e., 2.0 mol of API to 1.0mol fumaric acid). Nature of hydrogen bonding: fumaric acid was situatedin-between two molecules of Tabernanthalog via hydrogen bonds to theazepine (N1—O2, 2.70 Å) and indole nitrogen atoms (N2—O3, 2.81 Å).Crystal system 300(2): monoclinic (refer to Section 9.16.2, page 375)Space group 300(2): C2/c Unit cell 300(2) K: a = 21.7386(8) Å, b =9.7033(5) Å, c = 15.8640(8) Å, a = g = 900, b = 99.182(4)°, V =3303.4(3) Å³ Asymmetric unit: contained one molecule of API and halfmolecule of fumaric acid (crystal bonded). XRPD: 8.2°, 11.2°, 12.8°,15.5°, 17.0°, , 18.1°, 18.3°, 19.2°, 19.4°, 20.2°, 21.3°, 21.5°, 22.6°,23.7°, 24.3°, 24.8°, (2θ, 1 d.p), (refer to FIG. 377F) [Only peakswith >10% rel. intensity are provided.] DSC: onset 50.1° C. (−22.64Jg⁻¹, endotherm), 115.1° C. (−22.28 Jg⁻¹, endotherm) 183° C. (−14.73Jg⁻¹, endotherm) 210.7 (−111.8 Jg⁻¹, endotherm, melt) (5-B3, FIG. 377J).TGA (only ablations events): onset 75.9° C. (−1.2% w/w, solvent release)141.5° C. (−1.3% w/w, solvent release), 224.0° C. (−23.6% w/w, ablation)(FIG. 3771). ¹H NMR: (DMSO-d6, 400 MHZ); δ 10.6 (s, 1 H), 7.3 (d, J =8.6 Hz, 1 H), 6.8 (s, 1 H), 6.6 (dd, J = 8.6, 2.2 Hz, 1 H), 6.5 (s, 1H), 3.7 (s, 3H), 3.1-3.0 (m, 6 H), 2.9 (t, J = 9.9, 5.6 Hz, 2 H), 2.6(s, 3 H) conforms to the molecular structure (Σ19H*) (FIG. 377E).Residual solvents: 5-B3 (acetonitrile 0.3% w/w, ICH listed 410 ppm,acetone 0.2% w/w, ICH listed 5000 ppm and methanol, 2.4% w/w, ICH listed3000 ppm). *The molecular formula (C₁₈H₂₂N₂O₅) includes the carboxylicacid protons; however, they co-resonate with water.

G. Overall Conclusion

The tabernanthalog monofumarate salt Form A (unary fumarate, Pattern#6a), was prepared from water (anhydrous form, generated via suspensionequilibration in water at 20° C.). Form A was subsequently scaled up toafford batch 8-A4 (Experiment Reference 8-Sample Reference A4) (560 mg,56% th., yield uncorr.), to provide the control input for the saltscreen stability and solubility panels. Form B was also identified, fromacetonitrile; however, we were not able to obtain SC-XRD on this form.

In the presence of Form A, Form B slowly evolved into Form A undercompetitive suspension equilibration conditions. Metastable formsobtained via suspension equilibration and analyzed wet pellet, readilyunderwent conversion into Form A during drying. This supported theconclusion that Form A exhibited greatest relative stability amongst theforms identified. The hemi-fumarate salt was prepared andre-proportionated into the fumarate salt during an ageing cycle.Stability assessment of the supplied material (Pattern #1) at 40° C./75%RH executed over a 4-to-5-week period showed no evidence for hydrateformation, chemical degradation or disproportionation of the API.

Example 6: Salt Screen

Tabernanthalog is characterized to evaluate its physical properties. Theevaluation is performed by X-ray powder diffraction (XRPD), polarizedlight microscopy (PLM), differential scanning calorimetry (DSC),thermogravimetry (TG), dynamic vapor sorption/desorption (DVS), and/orsolubility testing in organic solvents, water, and mixed solventsystems. XRPD data are used to assess crystallinity. PLM data are usedto evaluate crystallinity and particle size/morphology. DSC data areused to evaluate melting point, thermal stability, and crystalline formconversion. TG data are used to evaluate if the free base is a solvateor hydrate, and to evaluate thermal stability. DVS data are used toevaluate hygroscopicity of the free base and if hydrates can be formedat high relative humidity. About 10 to 15 solvents are selected fromTable 188, based on their properties (polarity, dielectric constant anddipole moment).

TABLE 188 List of Solvents Used in Salt Screening Solvents acetic acidn-heptane Acetone n-hexane Acetonitrile1,1,1,3,3,3-hexafluoro-2-propanol benzyl alcohol isobutanol(2-methyl-1-propanol) 1-butanol isopentanol (3-methyl-1-butanol)2-butanol isopropyl alcohol (2-propanol) butyl acetate isopropylbenzene(cumene) t-butyl methyl ether Methanol Chlorobenzene methoxybenzene(anisole) Chloroform methyl acetate di(ethylene glycol) methyl ethylketone (2-butanone) Dichloromethane methyl isobutyl ketone diethyl etherNitromethane Diethylamine N-methyl-2-pyrrolidone (NMP) Dimethylacetamide(DMA) 1-octanol diisopropyl ether 1-pentanol N,N-dimethyl-formamide(DMF) 1-propanol dimethyl sulfoxide Perfluorohexane 1,4-dioxane propylacetate 1,2-ethanediol (ethylene glycol) 1,1,2,2-tetrachloroethaneEthanol Tetrahydrofuran Ethanolamine Toluene 2-ethoxyethanol(Cellosolve) 1,1,1-trichloroethane ethyl acetate 2,2,2-trifluoroethanolethyl formate Water formic acid o-xylene (1,2-dimethylbenzene) Glycerolp-xylene (1,4-dimethylbenzene)

The information obtained is used for designing the subsequent saltscreen. The salt screen is performed by reacting the free base withpharmaceutically acceptable acids under various conditions in attemptsto generate crystalline salts. Pharmaceutically acceptable acids thatmay be used are listed in Table 189 below. Specific acids are selectedbased on the pKa of the free base, and typically 15 to 20 acids areselected. Experiments are performed using 0.5 molar equivalent, 1 molarequivalent

TABLE 189 Exemplary Acids naphthalene-1,5-disulfonic acid citric acidsulfuric acid d-glucuronic acid ethane-1,2-disulfonic acid lactobionicacid p-toluenesulfonic acid D-glucoheptonic acid thiocyanic acid(−)-L-pyroglutamic acid methanesulfonic acid L-malic aciddodecylsulfuric acid hippuric acid naphthalene-2-sulfonic acidD-gluconic acid benzenesulfonic acid D,L-lactic acid oxalic acid oleicacid glycerophosphoric acid succinic acid ethanesulfonic acid, 2-hydroxyglutaric acid L-aspartic acid cinnamic acid maleic acid adipic acidphosphoric acid sebacic acid ethanesulfonic acid (+)-camphoric acidglutamic acid acetic acid pamoic (embonic) acid nicotinic acid glutaricacid, 2-oxo- isobutyric acid 2-naphthoic acid, 1-hydroxy propionic acidmalonic acid lauric acid gentisic acid stearic acid L-tartaric acidorotic acid fumaric acid carbonic acid galactaric (mucic) acid

Solvent systems for the salt crystallization experiments are selectedbased on the solubility of the free base and the selected acid. Solventsare used as a single solvent or as solvent mixtures, some containingwater. The techniques that are used for salt crystallization are chosenbased on the solvent selected and properties of the free base. Thefollowing techniques (or combination of techniques) may be used for saltcrystallization:

-   -   Free base and acid are dissolved in a solvent or mixture of        solvents, and the solvents are evaporated at different rates        (slow evaporation or fast evaporation) and at different        temperatures (ambient or elevated).    -   Free base and acid are dissolved in a solvent or mixture of        solvents (at ambient temperature or an elevated temperature),        and the final solution is cooled to a sub-ambient temperature        (between −78° C. to 15° C.). The cooling method can be a fast        cooling (by plunging the sample into an ice bath or a dry        ice/acetone bath), or slow cooling. The solids formed will be        recovered by filtration and dried (air dried or vacuum dried).    -   Free base and acid are dissolved in a solvent or mixture of        solvents, and an antisolvent is added to precipitate the salt.        The solids formed will be recovered by filtration and dried (air        dried or vacuum dried).    -   Free base and acid are added to a solvent or mixture of        solvents, where one or both components are not fully dissolved.        The slurry is agitated at different temperatures for a number of        days. The solids formed will be recovered by filtration and        dried (air dried or vacuum dried). The same experiment can be        also performed in solvent systems where the solvents are not        miscible.    -   Free base and acid are milled together (by mechanical milling or        by mortar and pestle), with a drop of solvent, or without any        solvent.    -   Free base and acid are melted together and cooled to various        temperatures using various cooling rates.    -   If an amorphous form of a salt is obtained, the amorphous salt        will be exposed to elevated humidity, or elevated temperature        (or combination of both), or solvent vapors at various        temperatures to form crystalline salts.

The stoichiometric ratio of acid to tabernanthalog, is confirmed by ¹HNMR, HPLC, or both as is known to those of ordinary skill in the art.

The salts obtained are analyzed by XRPD to determine if they arecrystalline and, if so, by DSC to see the melting point and by TG to seeif they are hydrated/solvated, and by 1H NMR spectroscopy to ensurechemical integrity. KF water titration is performed on salts that arehydrated. DVS analysis is performed to evaluate hygroscopicity of thesalt and if hydrated form is present.

Consistent with the methods above, the tabernanthalog salts listed inTable 190 were prepared and characterized.

TABLE 190 List of Prepared and Characterized Tabernanthalog Salts ¹H NMRMelting Consistent Salt XRPD Stoichiometry Point with Structure? SorbateFIG. 384 1.0 to 1.0 144° C. Yes Tartrate FIG. 385 1.0 to 1.0 208° C. YesMalate FIG. 386 1.0 to 1.0 131° C. Yes Tosylate FIG. 387 1.0 to 1.0 189°C. Yes Benzoate FIG. 388 1.0 to 1.0 183° C. Yes Adipate FIG. 389 1.0 to1.0 149° C. Yes Glucoronate FIG. 390 1.0 to 0.7 174° C. Yes PhosphateFIG. 391 — 207° C. Yes Edisylate FIG. 392 1.0 to 1 — Yes Free Base FIG.393 — 149° C. Yes Sulfate — — — Yes Maleate FIG. 394 1.0 to 1.0 — YesGalactarate FIG. 395 1.0 to 1.0 — Yes Citrate FIG. 396 1.0 to 0.9 — YesGlycolate FIG. 397 1.0 to 1.0 — Yes Succinate FIG. 398 1.0 to 0.4 — Yes

Example 7: Polymorph Screen of Tabernanthalog Salts

The active pharmaceutical ingredient (API), tabernanthalog, which may bea free base or a salt, is characterized to evaluate its physicalproperties. The evaluation is performed by X-ray powder diffraction(XRPD), polarized light microscopy (PLM), differential scanningcalorimetry (DSC), thermogravimetry (TG), dynamic vaporsorption/desorption (DVS), and/or solubility testing in organicsolvents, water, and mixed solvent systems. XRPD data are used to assesscrystallinity. PLM data are used to evaluate crystallinity and particlesize/morphology. DSC data are used to evaluate melting point, thermalstability, and crystalline form conversion. TG data are used to evaluateif the API is a solvate or hydrate, and to evaluate thermal stability.DVS data are used to evaluate hygroscopicity of the API and if hydratescan be formed at high relative humidity. About 10 to 15 solvents may beselected from the list provided in Table 191 below, based on theirproperties (polarity, dielectric constant, and dipole moment).

TABLE 191 List of Solvents Solvents acetic acid n-heptane acetonen-hexane acetonitrile 1,1,1,3,3,3-hexafluoro-2-propanol benzyl alcoholisobutanol (2-methyl-1-propano1) 1-butanol isopentanol(3-methyl-1-butanol) 2-butanol isopropyl alcohol (2-propanol) butylacetate isopropylbenzene (cumene) t-butyl methyl ether methanolchlorobenzene methoxybenzene (anisole) chloroform methyl acetatedi(ethylene glycol) methyl ethyl ketone (2-butanone) dichloromethanemethyl isobutyl ketone diethyl ether nitromethane diethylamineN-methyl-2-pyrrolidone (NMP) Dimethylacetamide (DMA) 1-octanoldiisopropyl ether 1-pentanol N,N-dimethyl-formamide (DMF) 1-propanoldimethyl sulfoxide perfluorohexane 1,4-dioxane propyl acetate1,2-ethanediol (ethylene glycol) 1,1,2,2-tetrachloroethane ethanoltetrahydrofuran ethanolamine toluene 2-ethoxyethanol (Cellosolve)1,1,1-trichloroethane ethyl acetate 2,2,2-trifluoroethanol ethyl formatewater formic acid o-xylene (1,2-dimethylbenzene) glycerol p-xylene(1,4-dimethylbenzene)The information obtained is used for designing the subsequent polymorphscreen. Solvents are used as a single solvent or as solvent mixtures,some containing water. The techniques used for the polymorph screen arechosen based on the solvent selected and properties of the API. Thefollowing techniques (or a combination of techniques) may be used forthe polymorph screening:

-   -   API is dissolved in a solvent or mixture of solvents, and the        solvents are evaporated at different rates (slow evaporation or        fast evaporation) and at different temperatures (ambient or        elevated).    -   API is dissolved in a solvent or mixture of solvents (at ambient        temperature or an elevated temperature), and the final solution        is cooled (between −78° C. to 20° C.). The cooling method can be        a fast cooling (by plunging the sample to an ice bath or a dry        ice/acetone bath), or slow cooling. The solids formed will be        recovered by filtration and dried (air dried or vacuum dried).    -   API is dissolved in a solvent or mixture of solvents, and an        antisolvent is added to precipitate the salt. The solids formed        will be recovered by filtration and dried (air dried or vacuum        dried).    -   API is added to a solvent or mixture of solvents, where the API        is not fully dissolved. The slurry will be agitated at different        temperatures for a number of days. The solids formed will be        recovered by filtration and (air dried or vacuum dried).    -   API is milled (by mechanical milling or by mortar and pestle),        with a drop of solvent, or without any solvent.    -   API is melted and cooled (at different cooling rates, fast and        slow, and cooled to different temperatures) to obtain solids.    -   API is suspended in a solvent or mixture of solvents, and the        slurry is placed in a heating/cooling cycle for multiple cycles.        The remaining solids after the final cooling cycle will be        filtered and (air dried or vacuum dried).    -   API is processed to obtain an amorphous form (by melting,        milling, solvent evaporation, spray drying or lyophilization).        The amorphous form will then be exposed to elevated humidity (or        elevated temperature, or combination thereof), or to solvent        vapors for extended period of days.    -   API is exposed to elevated humidity (or elevated temperature, or        combination thereof), or to solvent vapors for extended period        of days.    -   Two or more polymorphs of the API are mixed in a solvent or        solvent systems (some solvent mixtures containing variable        amount of water) to obtain a slurry, and the slurry will be        agitated (at various temperatures) for an extended period of        time (days). The solvent system used can be pre-saturated with        the API. The final solids will be filtered and dried (air dried        or vacuum dried).    -   API is heated to a specific temperature and cooled (at ambient        conditions or in a dry box).

The solids obtained are analyzed by XRPD to determine if they arecrystalline and, if so, by DSC to see the melting point and by TG to seeif they are hydrated/solvated, and by ¹H NMR spectroscopy to ensurechemical integrity. KF water titration is performed on forms that arehydrated. DVS analysis is performed to evaluate hygroscopicity of theform and if hydrated form is present. In particular, variabletemperature analyses, including variable temperature XRPD, are performedto assess the stability of each physical form as well as itscrystallinity.

Differential scanning calorimetry (DSC) thermograms are obtained using aDSC Q 100 (TA Instruments, New Castle, Del.). The temperature axis andcell constant of the DSC cell are calibrated with indium (10 mg, 99.9%pure, melting point 156.6° C., heat of fusion 28.4 J/g). Samples(2.0-5.0 mg) are weighed in aluminum pans on an analytical balance.Aluminum pans without lids are used for the analysis. The samples areequilibrated at 25° C. and heated to 250-300° C. at a heating rate of10° C./min under continuous nitrogen flow. TG analysis of the samples isperformed with a Q 50(TA Instruments, New Castle, Del.). Samples(2.0-5.0 mg) are analyzed in open aluminum pans under a nitrogen flow(50 mL/min) at 25° C. to 210° C. with a heating rate of 10° C./min.

The sample for moisture analysis is allowed to dry at 25° C. for up to 4hours under a stream of dry nitrogen. The relative humidity is thenincreased stepwise from 10 to 90% relative humidity (adsorption scan)allowing the sample to equilibrate for a maximum of four hours beforeweighing and moving on to the next step. The desorption scan is measuredfrom 85 to 0% relative humidity with the same equilibration time. Thesample is then dried under a stream of dry nitrogen at 80° C. for 2hours or until no weight loss is observed.

X-ray powder diffraction data are collected using a Miniflex TabletopXRD system (Rigaku/MSC, The Woodlands, Tex.) from 5° to 45° 2θ withsteps of 0.1°, and the measuring time is 1.0 second/step. All samplesare ground to similar size before exposure to radiation. The powdersamples are illuminated using CuKα radiation (λ=1.54056 Å) at 30 kV and15 mA.

Variable temperature XRPD data are collected using a Huber Imaging PlateGuinier Camera 670 employing N1-filtered CuKα₁ radiation (λ=1.5405981 Å)produced at 40 kV and 20 mA by a Philips PW1120/00 generator fitted witha Huber long fine-focus tube PW2273/20 and a Huber Guinier MonochromatorSeries 611/15. The original powder is packed into a Lindemann capillary(Hilgenberg, Germany) with an internal diameter of 1 mm and a wallthickness of 0.01 mm. The sample is heated at an average rate of 5Kmin⁻¹ using a Huber High Temperature Controller HTC 9634 unit with thecapillary rotation device 670.2. The temperature is held constant atselected intervals for 10 min while the sample is exposed to X-rays andmultiple scans were recorded. A 2θ-range of 4.00-100.0° is used with astep size of 0.005° 2θ.

In certain embodiments wherein the solid form is a solvate, such as ahydrate, the DSC thermogram reveals endothermic transitions. Inaccordance with the observed DSC transitions, TGA analysis indicatesstages of weight change corresponding to desolvation or dehydrationand/or melting of the sample. In the case of hydrates, these results arein harmony with Karl Fisher titration data which indicate the watercontent of the sample.

The moisture sorption profile of a sample can be generated to assess thestability of a solid form is stable over a range of relative humidities.In certain embodiments, the change in moisture content over 10.0 to95.0% relative humidity is small. In other embodiments the change inmoisture content over 10.0 to 95.0% relative humidity is reversible.

In certain embodiments, the XRPD pattern of a sample of solid formindicates that the sample has a well-defined crystal structure and ahigh degree of crystallinity.

Example 8: Salt Screen of Tabernanthalog List of Abbreviations

-   a_(w) Water activity-   ASD Amorphous solid dispersion-   ca. circa, approximately-   cf to confer, to compare-   ° C. degree Celsius, absolute temperature-   CP Chemical Purity-   CP Cross-polarized light-   CP-MAS Cross Polarized Magic Angle Spinning (¹³C NMR solid state    technique)-   CPME Cyclopentyl methyl ether-   Da Dalton-   DCM Dichloromethane-   DF Dilution factor-   DiPE Diisopropyl ether-   DMSO Dimethyl Sulfoxide-   DSC Differential Scanning Calorimetry (measures changes in heat    capacity)-   DTA Differential Thermal Analysis (measures changes in temperature)-   DVS Dynamic Vapour Sorption (used interchangeably with GVS)-   e.g. for example-   etc. etcetera-   FaSSIF Fasted State Simulated Intestinal Fluid-   FeSSIF Fed State Simulated Intestinal Fluid-   FaSSGF Fasted State Simulated Gastric Fluid-   FT-IR InfraRed spectroscopy (prefixed mid and far)-   g gram(me)-   GRAS Generally Recognised As Safe-   GVS Gravimetric Vapour Sorption-   h hour-   HPLC High Performance Liquid Chromatography-   HSM Hot Stage Microscopy-   i.e. that is-   IPA Isopropyl alcohol-   IPrOAc Isopropyl acetate; sometimes abbreviated to IPAc-   J Joule-   K Degrees Kelvin. Si unit of temperature, used interchangeably    with° C. to express increment/decrement rate of change of    temperature set point (e.g. ramp rate on DSC thermogram 10 K/min);    note K sign not prefixed by °-   KF Karl Fischer (aquametry, determination of the water content by    coulometric titration)-   kg kilogram(me)-   l litre-   LOD Loss On Drying-   mag magnification-   mAu milli Absorption units (chromatographic unit of peak height)-   mAu*s milli Absorption units multiplied by second (chromatographic    unit of peak area)-   MEK Methyl ethyl ketone (butanone)-   MET/CR Aptuit QC chromatography method reference-   Me-THF 2-Methyltetrahydrofuran-   min. minute-   mg milligram(me)-   ml millilitre-   mol mole, amount of substance-   N/A Not Applicable-   n.a. not analysed-   n.d. not detected-   nm nanometre-   NMP N-Methyl-2-Pyrrolidone-   NMR Nuclear Magnetic Resonance (heteronuclear, prefixed by the    stable isotope under-   analysis: ¹³C, ¹⁹F, ¹H and ³¹P)-   NP non-polarized-   oab on anhydrous basis-   oasfb on anhydrous solvent free basis-   osfb on solvent free basis-   PGI Potential genotoxic impurity-   pH −log [H⁺] or pH=−log a_(H) ⁺-   pK_(a) −log (K_(a)), acid dissociation constant-   pI isoelectric point, quoted in unit pH-   PLM Polarized Light Microscopy-   Rel RT Relative Retention Time (not be confused RT)-   REP/Aptuit report (REP) reference-   RFA Request For Analysis (unique reference number)-   RH Relative Humidity (a_(w)*100)-   RT Room Temperature (ambient, typically: 18 to 23° C.)-   s second-   SCXD Single Crystal X-Ray Determination-   SIF Simulated Intestinal Fluid-   STA Simulated Thermal Analysis (STA=TGA+DTA)-   t time in seconds, minutes, hour, days etc. (interval specified in    parentheses); alias is in common use metric tonne (t)-   t Tonne, metric unit of mass (1000 kg; 1 mg), (compaction force in    kg, suffixed in parentheses)-   T Temperature recorded in degrees Celsius (° C.); alias is in common    use, SI unit of magnetic flux density, also denoted T-   tBME tert-Butyl methyl ether-   TCNB 2,3,5,6-Tetrachloronitrobenzene (C₆HCl₄NO₂, F.W. 260.89    gmol⁻¹V); used as an internal stand for Q ¹H NMR assay-   TFE Trifluoroethanol-   TGA Thermogravimetric Analysis-   th. theoretical-   UV Ultra Violet-   vol volume-   W Watt-   w/w weight/weight-   vs. versus-   v/v volume/volume-   XRPD X-Ray Powder Diffraction

Counter Ion Abbreviations

-   EDS Ethanesulfonic acid-   MSA Methanesulfonic acid-   TSA 4-Toluenesulfonic acid

List of Definitions

-   Amorphous Exhibits no long-range crystal order and displays a    diffuse noise halo X-ray diffraction pattern.-   Cross polarized light Light passed through two polaroid filters    orientated at ninety degrees to one another.-   Habit (crystal) Different crystal size or shape.-   Native Refers to an API in its native or non-ionised form.-   Normal light Vibrates in all directions perpendicular to the axis to    which the light travels.-   Particle size Expressed as probability distribution, i.e., the range    D10>PSD<D90 captures the sizes of 80% of the particles.-   Plane polarized light Light passed through a polaroid filter which    allows light vibrating in one plane to be transmitted.-   Polymorphism Crystalline solid able to exhibit different crystalline    phases.-   Photomicrograph Imaged captured of a small object under    magnification through an optical microscope.-   Pseudopolymorphism Different crystal structure attributed to the    incorporation of molecular water or solvent.-   Solvates Contains a molecule of solvent in the crystal lattice.-   Thermogram Differential scanning calorimetry trace: heat flow on    y-ordinate (mW), time (minutes)/temperature (° C.) on x-ordinate.

A. Study Overview

This study describes the salt screen performed on theAPI(tabernanthalog, native, non-ionized form). It covers theaccompanying physicochemical evaluations that enabled nomination of apreferred salt form, i.e., The tabernanthalog sorbate salt (API tocounter-ion ratio, 1 to 1).

b. Objectives

The objectives of this study of the salt screen are (a) to identify andcharacterize a fit for purpose salt form of Tabernanthalog, that isstable, crystalline, and exhibit improved physicochemical properties,compared to the native form, and (b) to demonstrate that the selectedsalt form is suitable for development scale-up.

C. Summary

Tabernanthalog (native) (non-ionized form, free base) was supplied as acrystalline solid (FIG. 393 and Table 215) and exhibited a single meltevent evident by DSC (m.p 149° C., FIG. 439 ). The non-ionized form wasfreely soluble in most common solvents investigated at 20° C., apartfrom tBME, heptane and water (Experiment 1 and Table 198).

The non-ionized form of Tabernanthalog was screened against 23 common,Classes 1, 2 and 3 acidic counter-ions in selected solvents. The APIdelivered multiple hits (Experiment 2). Those salt forms that exhibitedmultiple thermal events by DSC and TGA, prior to deflagration weredeprioritized (these activities often indicate that solvatomorphism orpolymorphism complications may be present).

Salt selection was driven by the following desirable characteristics:(a) unique powder diffraction pattern by XRPD (this also confirmssalification as the powder diffraction pattern should not match the freebase API or the acid used), (b) flat baseline leading to single meltevent by DSC, (c) flat baseline up to the melt by TGA, (d) significantlyreduced impurity burden and absence of trace solvents by ¹H NMR(stoichiometry should also be 1 to 1 ratio API to acid), and (e)optically crystalline and reasonably equant morphology undercross-polarized filter.

Based on the above criteria, the front-runner salt forms were thetabernanthalog sorbate salt, the tabernanthalog tartrate salt, thetabernanthalog malate salt, and the tabernanthalog benzoate salt.

This set of API salts were obtained as 1 to 1 ratio and weresubsequently subjected to physicochemical studies that included: (a)solubility determination in FaSSIF, FeSSIF and FaSSGF buffers and the pHadjusted after each time point (Experiment 5), (b) stability evaluationat 40° C./75% RH for 10 days (the Equilibrium Humidity EvaluationExperiment) (no hydrate formation observed), and (c) DVS analyses (massequilibrated, the Dynamic Vapour Sorption (DVS) Study).

The above studies concluded that the tabernanthalog sorbate salt was thepreferred candidate as it exhibited much higher crystallographic qualitythan the tabernanthalog monofumarate salt. The is a key physicalattribute required in later screening. Because the tabernanthalogsorbate salt exhibited a higher crystallographic quality, it is expectedto provide greater solvent and impurity rejection and give overallbetter performance in advanced physicochemical screening. Furthermore,the chemical purity did not reduce significantly during stability, thesalt was highly soluble in the SIF buffers examined anddisproportionation was not observed. It is noted that sorbic acid isGRAS and is used as a food additive.

The tables of characterization are provided in Tables 192-194.

TABLE 192 The Tabernanthalog Sorbate Salt Provenances of referencebatches The tabernanthalog sorbate salt (Form A) 2-V2 (ExperimentReference batches: 2-V2 (Experiment Reference 2-Sample Reference V2),Reference 2- 3-C1 (Experiment Reference 3-Sample Reference C1), 4-A2(Experiment Sample Reference Reference 4-Sample Reference A2) V2):obtained from Molecular weight: 342.439 g.mol⁻¹ heat-up/cool- Exactmolecular weight: 342.1943 down Molecular formula: C₂₀H₂₆N₂O₃crystallization of Unary sorbate: 24.7% w/w th., sorbic acid (i.e., 1.0mol of API to 1.0 mol Tabernanthalog sorbic acid) (native) with SCXRD:Unary/mono sorbate. The simulated powder pattern, predicted sorbic acidin from single crystal structure at 100K agreed with the experimentallyethanol (5.0 vol) at observed Form A powder pattern obtained at 298K.85° C. The product Nature of hydrogen bonding: Hydrogen bonding betweenboth oxygen was isolated by molecules on the sorbate ion. One to N1(tryptamine nitrogen atom) of one centrifugation and API molecules, theother to N2 (hydro-azepine nitrogen atom) of a separate was oven-driedAPI molecule. Due to hydrogen bonding present in the structure builds upunder reduced chains between API and salt molecule. Causing stacking ofAPI and sorbate pressure over 20 h molecules closely packed to oneanother. This leads to less free space in the at 40° C. crystalstructure and void radius of only ~0.9 A, much smaller than the 1.4 3-C1(Experiment required for a water molecule to occupy. Bond betweenSorbates and API, Reference 3- N1—O3, 2.857 Å (hydrogen bond), N2—O2,2.7015 Å (salification Sample Reference hydrogen bond) C1): same as N1 =Indole, N2 = Hydroazepine. above. However, Sorbate molecule isdisordered and bond lengths stated are an average of dissolution was thetwo mapped positions. achieved in ethanol Crystal system 100(2) K:monoclinic (3.0 vol) and was Space group 100(2) K: P2₁/c isolated byUnit cell 100(2) K: a = 9.3410(3) Å, b = 6.4173(2) Å, c = 30.5108(12) Å.filtration and dried A = γ = 90° ß = 95.374(3)°, V = 1820.90(11) Å3.under sustained Asymmetric unit: contains one API molecule one sorbateion. nitrogen flux (<1 XRPD: 5.7°, 10.5°, 11.4°, 17.9°, 18.8°, 19.1°,21.4°, 22.6°, 22.9°, 24.4°, bar) over 20 h at 24.7°, 26.8° (2θ, 1 d.p)[(2-V2), FIG. 384 and Table 216]. 20° C. DSC: onset 143.9° C. (−84.1Jg⁻¹, endotherm, melt) [(2-V2), FIG. 453]. 4-A2 (Experiment TGA: onset171.8° C. (−26.0% w/w, ablation) 250.0° C. (−19.9% w/w, Reference 4-ablation) [(2-V2), FIG. 454]. Sample Reference DVS 0 to 90 to 0% RH(dm/dt <0.002%): 0.0 (0.00%), 5.0 (0.0%), 10.0 A2): same as 3-C1(0.01%), 15.0 (0.01%), 20.0 (0.02%), 25.0 (0.03%), 30.0 (0.03%), 40.0(Experiment (0.05%), 50.0 (0.07%), 60.0 (0.10%), 70.0 (0.14%), 80.0(0.21%), 90.0 Reference 3- (0.98%), 90.0 (0.98%), 80.0 (0.48%), 70.0(0.30%), 60.0 (0.18%), 50.0 Sample Reference (0.06%), 40.0 (0.03%), 30.0(0.00%), 25.0 (−0.007%), 20.0 (−0.02%), 15.0 C1). (−0.03%), 10.0(−0.04%), 5.0 (−0.05%), 0.0 (−0.06%) [(4-A2), FIG. 455 and 456]. UVchromatographic purity: 99.64% area (212 nm), [(4-A2), FIG. 566]. ¹HNMR: (DMSO-d6, 400 MHz); δ 10.4 (s, 1 H), 7.2 (d, J = 9.4 Hz, 1 H), 7.1(dd, J = 15.4, 9.6 Hz 1 H), 6.7 (d, J =2.3 Hz, 1 H), 6.6 (dd, J = 8.5,2.2 Hz, 1 H), 6.3-6.2 (m, 2 H), 5.8 (d, J = 15.4 Hz, 1 H), 3.7 (s, 3 H),2.9-2.7 (m, 8 H) 2.4 (s, 3 H), 1.8 (d, J = 5.9 Hz, 3 H) conforms to themolecular structure (Σ25H*), (Experiment 4-A2, FIG. 562). Residualsolvents ICH Q3C (R8): 4-A2 (ethanol 0.1% w/w); 3-C1 (ethanol 0.3% w/w);2-V2 (ethanol 0.1% w/w, ICH listed 5000 ppm). Appearance: columnar,prismatic crystals, [(4-A2), FIG. 567-572]. Solubility in SIF buffers:Insoluble in FeSSIF at 37° C. up to 1 h. Insoluble in FaSSGF at 37° C.up to 24 h. *The molecular formula (C₂₀H₂₆N₂O₃) includes the carboxylicacid proton that is not detected by ¹H NMR

TABLE 193 The Tabernanthalog Tartrate Salt Provenances of referencebatches The tabernanthalog tartrate salt 2-12 (Experiment Referencebatches: 2-I2 (Experiment Reference 2-Sample Reference I2), Reference 2-3-A1 (Experiment Reference 3-Sample Reference A1) Sample ReferenceMolecular weight: 380.397 g.mol⁻¹ I2): obtained from Exact molecularweight: 380.1583 heat-up/cool-down Molecular formula: C₁₈H₂₄N₂O₇crystallization of Unary tartrate: 39.5% w/w th., L-tartaric acid (i.e.,1.0 mol of API to 1.0 Tabernanthalog mol tartaric acid) (native) with L-XRPD: 16.1°, 16.49°, 17.3°, 18.2°, 19.9°, 20.4°, 21.3°, 22.4°, 24.0°,24.3°, tartaric acid in 26.1°, 26.8°, 28.3°, 32.6°, 32.9°, 34.3°, 37.8°,38.1° (2θ, 1 d.p) [(2-12), ethanol (11.2 vol) FIG. 385 and Table 217].and water (7.2 vol) DSC: onset 208.2° C. (−137.2 Jg⁻¹, endotherm, melt)[(2-12), FIG. 469]. at 85° C. The TGA: onset 219.3° C. (−56.1% w/w,ablation) 322.1° C. (−9.5% w/w, product was isolated ablation) [(2-12),FIG. 470]. by centrifugation DVS 0 to 90 to 0% RH (dm/dt <0.002%): 0.0(0.00%), 5.0 (0.01%), 10.0 and was oven-dried (0.02%), 15.0 (0.04%),20.0 (0.05%), 25.0 (0.07%), 30.0 (0.10%), 40.0 under reduced (0.16%),50.0 (0.24%), 60.0 (0.34%), 70.0 (0.48%), 80.0 (0.72%), 90.0 pressureover 20 h at (1.34%), 90.0 (1.34%), 80.0 (0.75%), 70.0 (0.51%), 60.0(0.37%), 50.0 40° C. (0.27%), 40.0 (0.20%), 30.0 (0.13%), 25.0 (0.11%),20.0 (0.08%), 15.0 3-A1 (Experiment (0.07%), 10.0 (0.04%), 5.0 (0.03%),0.0 (0.02%) [(3-A1) FIGS. 471 and Reference 3- 472]. Sample Reference UVchromatographic purity: 99.58% area (212 nm) [(3-A1) FIG. 476]. A1):same as above, ¹H NMR: (DMSO-d6, 400 MHz); δ 10.6 (s, 1 H), 7.3 (d, J =8.2 Hz, 1 H), however, dissolution 6.8 (d, J = 2.3 Hz, 1 H), 6.6 (dd, J= 8.7, 2.2 Hz, 1 H), 4.0 (s, 2 H), 3.7 (s, 3 was achieved in H), 3.1-3.0(m, 6 H), 2.9 (t, J = 10.6, 5.6 Hz, 2 H), 2.6 (s, 3 H) conforms ethanol(5.0 vol) and to the molecular structure (Σ20H*), [(3-A1) FIGS. 545 and546]. water (5.75 vol) at Residual solvents ICH Q3C (R8): 3-A1 (ethanol0.05% w/w); 2-I2 85° C. Product was (ethanol 0.1% w/w, ICH listed 5000ppm). isolated by filtration Appearance: non-homogeneous plates, [(3-A1)FIGS. 477-482]. and dried under Solubility in SIF buffers: Soluble inall SIF buffers at 37° C. during 24 h. sustained nitrogen flux (<1 bar)over 20 h at 20° C. *The molecular formula (C₁₈H₂₄N₂O₇) includes thehydroxyl and carboxylic acid protons that are not detected by ¹H NMR.

TABLE 194 The Tabernanthalog Benzoate Salt Provenances of referencebatches Tabernanthalog• Benzoate 2-R2 (Experiment Reference batches:2-R2 (Experiment Reference 2-Sample Reference R2), Reference 2- 3-B1(Experiment Reference 3-Sample Reference B1) Sample Reference Molecularweight: 352.43 g.mol⁻¹ R2): obtained from Exact molecular weight:352.1786 heat-up/cool- Molecular formula: C₂₁H₂₄N₂O₃ down Unarybenzoate: 34.6% w/w th., benzoic acid (i.e., 1.0 mol of API to 1.0crystallization of mol benzoic acid) Tabernanthalog XRPD: 9.00°, 14.1°,15.6°, 16.7°, 17.7°, 18.1°, 19.6°, 21.3°, 22.9°, 23.7°, (native) with24.4°, 26.3°, 28.9° (2θ, 1 d.p), [(2-R2) FIG. 388 and Table 218].benzoic acid in DSC: onset 186.0° C. (−107.1 Jg-1, endotherm, melt)[(3-B1) FIG. 552]. ethanol (8.4 vol) TGA: onset 205.3° C. (−54.5% w/w,ablation) [(3-B1) FIG. 556]. and water (1.4 vol) DVS 0 to 90 to 0% RH(dm/dt <0.002%): 0.0 (0.00%), 5.0 (−0.001%), at 85° C. The 10.0(0.002%), 15.0 (−0.002%), 20.0 (−0.003%), 25.0 (−0.002%), 30.0 productwas (0.002%), 40.0 (0.002%), 50.0 (0.006%), 60.0 (0.009%), 70.0(0.009%), isolated by 80.0 (0.046%), 90.0 (0.118%), 90.0 (0.118%), 80.0(0.063%), 70.0 centrifugation and (0.034%), 60.0 (−0.001%), 50.0(−0.014%), 40.0 (−0.018%), 30.0 was oven-dried (−0.023%), 25.0(−0.028%), 20.0 (−0.029%), 15.0 (−0.032%), 10.0 under reduced (−0.032%),5.0 (−0.034%), 0.0 (−0.037%) [(3-B1) FIGS. 486(A) and pressure over 20 h486(B)]. at 40° C. UV chromatographic purity: 99.23% area (212 nm),(3-B1) Figure 3-B1 (Experiment 486(E)]. Reference 3- ¹H NMR: (DMSO-d6,400 MHz); δ 10.0 (s, 1 H), 7.9 (dd, J = 8.0, 1.0 Hz, Sample Reference 2H), 7.6 (td, J = 14.7, 7.2, 2.6, 1.1 Hz, 1 H), 7.5 (t, J = 15.1, 7.8 Hz,1 H), B1): same as 7.2 (d, J=8.6 Hz, 1 H), 6.7 (d, J = 8.6, 2.2 Hz, 1H), 3.7(s, 3 H), 2.9-2.8 (m, above, however, 2 H), 2.8-2.7 (m, 6 H), 2.4(s, 3 H) conforms to the molecular structure dissolution was (Σ23H*)[(3-B1) FIGS. 547 and 548]. achieved in ethanol Residual solvents ICHQ3C (R8): 3-B1 (ethanol 0.3% w/w); 2-R2 (5.0 vol) and water (ethanol0.1% w/w, ICH listed 5000 ppm). (0.85 vol) at 85° C. Appearance: [(3-B1)FIGS. 486(F)-486(K)]. Product was Solubility in SIF buffers: Soluble inall SIF buffers at 37° C. during 24 h. isolated by filtration and driedunder sustained nitrogen flux (<1 bar) over 20 h at 20° C. *Themolecular formula (C₂₁H₂₄N₂O₃) includes the carboxylic acid proton thatis not detected by ¹H NMRd. SALT SCREEN

The objective of the salt screen was to identify a pharmaceuticallyacceptable crystalline salt form of the API. In addition, the electedsalt form should exhibit appropriate physicochemical properties andshould possess relevant toxicological considerations that are judgedsuitable for development scale-up. Additionally, a preliminary processto access the elected salt form was evaluated.

The pKa of Tabernanthalog was calculated (cpKa) using MarvinSketch20.21.0 from ChemAxon Ltd. Compounds most suited to salification containan ionizable functional group at least 3 pKa units removed from thecounter-ions being screened. Non-ionized Tabernanthalog has cpKa of 8.0on the azepine nitrogen, while the indole nitrogen is assumed to benon-ionizable in both compounds (FIG. 399 ).

The counter ions for the salt screened were selected based on theirtheoretical pK_(a) values. The initial screen was carried out againstca. 22 acids (refer to Table 195, Table 196, Table 197).

TABLE 195 Class 1 counter ions proposed for salt screen onTabernanthalog. pKa Value REAGENT pK_(a) 1 pK_(a) 2 pK_(a) 3 EXAMPLE USEHydrochloric −6.0 — — Nearly half of all salts of acid basic drugsubstances Sulfuric acid −3.0 1.9 — Amphetamine sulfate Maleic acid 1.96.2 — Bromophenir-amine maleate, chlorpheniramine maleate (OTC)Phosphoric 1.9 7.1 12.3 Codeine Phosphate, acid clindamycin phosphate(+)-L-Tartaric 3 4.4 — Zolpidem tartrate, Brimonidine acid tartrate,Revastigmine tartrate Fumaric acid 3 4.4 — Ketotifen fumarate (OTC),Clemastine fumarate (OTC) Galactaric 3.1 3.6 — Quinidinepolygalacturonate acid Citric acid 3.1 4.8 6.4 Sildenafil citrate,Tamoxifen citrate, Azithromycin citrate D-Glucuronic 3.2 — —Trimetrexate glucuronate, acid Neutrexin Glycolic acid 3.3 — — —(−)-L-Malic 3.5 5.1 — Acetophenazine maleate, acid Pheniramine maleate,Chlorheniramine maleate D-Gluconic 3.8 Chlorhexidine gluconate, acidQuinidine gluconate L-Lactic 3.9 — — Haloperidol lactate L-Ascorbic 4.2— — Vascor acid Succinic acid 4.2 — — Desvenlafaxine succinate, Loxapinesuccinate, Sumatriptan succinate Acetic acid 4.8 — — Hydrocortisoneacetate, Desmopressin Adipic acid 4.4 5.4 fatty acid metabolite Sorbicacid 4.7 food-grade preservative

TABLE 196 Class 2 counter ions proposed for salt screen onTabernanthalog pKa Value REAGENT pKa 1 pKa 2 pKa 3 EXAMPLE USEp-Toluenesulfonic acid* −1.3 — — — Methanesulfonic acid*   2.1 — —Almitrine, anatzoline Ethane sulfonic acid*   2.05 — — Ergotoxine,dihydroergocornine Benzoic acid   4.2 Rizatriptan benzoate,Betamethasone benzoate *PGI risk, in conjunction with alcohols.

TABLE 197 Class 3 counter ions proposed for salt screen onTabernanthalog. pK_(a) Value REAGENT pK_(a) 1 pK_(a) 2 pK_(a) 3 EXAMPLEUSE Hydrobromic acid −9.0 — — Citalopram, lithium

i. Targeted Solubility of Tabernanthalog in Common Solvents (Experiment1)

The approximate solubility of Tabernanthalog (native) was determined invarious solvents at room temperature, 40° C. and at reflux. Thesolutions were observed after cooling to determine if crystallizationoccurred on standing at room temperature.

This study provided essential solubility information, necessary toselect appropriate solvents to undertake the salt screen. The solubilityof Tabernanthalog (native) was assessed against 19 common solvents. TheAPI, Tabernanthalog (native) was soluble in 16 solvents at reflux(various volumes) and solid was observed upon cooling (Table 198).Exceptions were tBME, heptane and water.

By analogy with the solubility properties of the tabernanthalogmonofumarate salt, ethanol was selected as the initial solvent to use inthe salt screen [1-F1 (Experiment Reference 1-Sample Reference F1),Table 198].

ii. Heat-Up Cool-Down Crystallization Salt Screen (Experiment 2)

Evidence of salt formation in the solid state was provided by thefollowing analyses (a) presentation of a unique powder diffractionpattern, that exhibited significant differences from the powder patternsof Tabernanthalog (native), the native acid counterion (also assumednon-ionized) and importantly, was non-congruent with the sum of theirreflections, (b) presence of integer stoichiometry of the counterionwith respect to tabernanthalog (native) and a measurable change in thechemical shift (S values), of the relevant ionizable proton resonances,by solution ¹H NMR, and (c) change in the temperature of fusion and ΔHfusion by DSC, compared to the values exhibited by Tabernanthalog(native) and the acid counterion.

TABLE 198 Targeted solubility screen of Tabernanthalog (native) incommon solvents. Experiment 5 vol 10 vol 15 vol Reference- Solid SolidSolid Sample ICH Solution at on Solution at on Solution at on ReferenceSolvent Class 20° C. 40° C. Reflux cooling 20° C. 40° C. reflux cooling20° C. 40° C. reflux cooling 1-A Acetone 3 x x ✓ Yes 1-B Acetonitrile 2x x x − x x ✓ Yes 1-C terl-Butylmethyl 3 x x x − x x x − x x x − ether1-D Chlorobenzene 2 x x ✓ Yes 1-E Dichloromethane 2 x x ✓ Yes 1-FEthanol 3 x x ✓ Yes 1-G Ethyl acetate 3 x x x − x x ✓ Yes 1-H Ethylformate 3 x x x − x x ✓ Yes 1-I Heptane 3 x x x − x x x − x x x 1-JIsopropyl acetate 3 x x x − x x x − x x ✓ Yes I-K Methanol 2 x x ✓ Yes1-L Methyl acetate 3 x x x − x x ✓ Yes 1-M Methylethyl 3 x x ✓ Yesketone 1-N 2-Methyl THF # x x ✓ Yes 1-O Nitromethane 2 x x ✓ Yes 1-P2-Propanol 3 x x ✓ Yes 1-Q Tetrahydrofuran 2 x x ✓ Yes 1-R Toluene 2 x xx − x x x − x x ✓ Yes 1-S Water # x x x − x x x − x x x Experiment 20vol Reference- Solid Sample Solution at on Reference 20° C. 40° C.reflux cooling 1-A 1-B 1-C x x x − 1-D 1-E 1-F 1-G 1-H 1-I x x x − 1-JI-K 1-L 1-M 1-N 1-O 1-P 1-Q 1-R 1-S x x x −

Priority was given to those salts that exhibited good crystallinity andlittle obvious disordering by XRPD, a flat DSC baseline in conjunctionwith a single sharp melt event and negligible weight loss, prior todeflagration by TGA, were also considered to be desirablecharacteristics. The analytical data of the rejected salt forms arereported in FIGS. 529, 394-398 , and 535-544 and Tables 225-229.

Five anhydrous, solvent free, single melt, stable forms of salifiedTabernanthalog were identified (i.e. 1.0 mol of API to 1.0 molstoichiometry salts (green shaded entries in Table 199), in conjunctionwith a suitable stable form of the tabernanthalog monofumarate salt(Pattern #6a (Form A), for example, Table 185 of Example 5). Morespecifically, the tabernanthalog sorbate salt (2-V2 or ExperimentReference 2-Sample Reference V2), The tabernanthalog tartrate salt (2-I2or Experiment Reference 2-Sample Reference I2), The tabernanthalogmalate salt (2-02 or Experiment Reference 2-Sample Reference O2) and Thetabernanthalog benzoate salt (2-R2 or Experiment Reference 2-SampleReference R2) were selected and progressed through into thephysicochemical evaluation, using the tabernanthalog monofumarate salt(Pattern #6a, Form A, 8-A4 (Experiment Reference 8-Sample Reference A4)of Example 5 above), as the control. The entries not reported in Table199 did not crystallize and remained as solutions at sub-ambienttemperature.

The tabernanthalog sorbate salt (2-V2 (Experiment Reference 2-SampleReference V2), FIGS. 451-466 and Table 216) was highly crystalline byXRPD analysis and exhibited unique powder diffraction pattern (FIG. 400). Negligible change in the impurity burden was observed in aryl andaliphatic regions (FIG. 451 ). Sharp melt (onset 144° C.) was observedas shown in FIG. 453 (non-ionized Tabernanthalog (m.p. 149° C.) andsorbic acid (m.p. 135° C.), as well as a flat TG baseline (FIG. 454 ).

The tabernanthalog tartrate salt (2-I2 (Experiment Reference 2-SampleReference I2), FIGS. 467-482 and Table 217) showed a highly crystallinepowder diffraction pattern that was different from Tabernanthalog(native) and L-tartaric acid (FIG. 401 ). ¹H NMR analysis exhibited adecrease in the impurity burden was observed in aryl and aliphaticregions (FIG. 467 ).

The specimen exhibited sharp, single melt event (208° C.) as shown inFIG. 469 (non-ionized Tabernanthalog (m.p. 149° C.) and L-tartaric acid(m.p. 169° C.)), and a flat TG baseline prior ablation (FIG. 470 ).

The tabernanthalog malate salt (2-02 (Experiment Reference 2-SampleReference O2), FIGS. 488-492 and Table 219) was highly crystalline withsharp, well resolved reflections and a unique powder diffraction pattern(FIG. 402 ). A small increase in the impurity burden in aryl andaliphatic regions was observed in the ¹H NMR spectrum of 2-O2 (FIG. 488). The thermogram exhibited a sharp melt event (131° C.) as shown inFIG. 490 (non-ionized Tabernanthalog (m.p. 149° C. and malic acid (m.p.130° C.)), and TGA showed a flat baseline (FIG. 491 ).

TABLE 199 Experiment 2 Results from salt screen on Tabernanthalog. Thefive salt forms highlighted in dark green were nominated for scale-up.Experiment Flat ¹H NMR Solvent Acceptable Reference- Flat Discretebaseline concordant ¹H NMR (ICH pharma- Sample baseline melt pre-meltwith (impunity Unique listed < Salt ceutical Salt Reference Salt (DSC)?(DSC)? (TGA)? structure? burden)? XRPD? 5000 ppm) stoichiometry saleform? class 2-V2 Tabernanthalog · ✓ ✓ ✓ ✓ Reduced ✓ 0.1% 1.0 to 1.0 ✓ 1Sorbate 2 -I2 Tabernanthalog · ✓ ✓ ✓ ✓ Reduced ✓ 0.1% 1.0 to 1.0 ✓ 1Tartrate 2-O2 Tabernanthalog · ✓ ✓ ✓ ✓ Maintained ✓ 0.2% 1.0 to 1.0 ✓ 1Malate 2-E2 Tabernanthalog · ✓ ✓ ✓ ✓ Reduced ✓ 0.1% 1.0 to 1.0 ✓ 2Tosylate 2-R2 Tabernanthalog · ✓ ✓ ✓ ✓ Reduced ✓ 0.1% 1.0 to 1.0 ✓ 2Benzoate 2-U2 Tabernanthalog · ✓ ✓ x ✓ Reduced ✓ 0.3% 1.0 to 1.0 ✓ 1Adipate 2-M2 Tabernanthalog · ✓ ✓ ✓ ✓ Elevated ✓ 0.2% 1.0 to 0.7 ✓ 1Glucuronate 2-H2 Tabernanthalog · ✓ ✓ x ✓ Elevated Disordered 0.3% Not ✓1 Phosphate determined 2-J2 Tabernanthalog · x x x ✓ Reduced Disordered0.4% 1.0 to 1.1 ✓ 2 Edisylate 2-C2 Tabernanthalog · x x — ✓ Not acquiredAmorphous — — ✓ 1 Sulfate 2-G2 Tabernanthalog · x x x ✓ ReducedDisordered 3.7% 1.0 to 1.0 ✓ 1 Maleate 2-K2 Tabernanthalog · x x ✓ ✓Reduced v. Disordered 0.1% 1.0 to 1.0 ✓ 1 Galactarate 2-L2Tabernanthalog · x x x ✓ Reduced v. Disordered 2.2% 1.0 to 0.9 ✓ 1Citrate 2-N2 Tabernanthalog · x x x ✓ Reduced Glucuronic 8.5% 1.0 to 1.0✓ 1 Glycolate acid 2-S2 Tabernanthalog · x x x ✓ Reduced ✓ 2.3% 1.0 to0.4 ✓ 1 Succinate Front-runner Deprioritised salt salt forms formsBack-up salt forms Undesirable characteristic

The tabernanthalog tosylate salt's (2-E2 (Experiment Reference 2-SampleReference E2), FIGS. 493-496A and Table 220) diffractogram was alsounique (FIG. 403 ) and highly crystalline by XRPD, with low anglereflection dominated, probably due to particle effects. It is noted thatdiffraction pattern should improve with increased powder averaging. ¹HNMR analysis showed a small decrease in the impurity burden in aryl andaliphatic regions (FIG. 493 ). DSC thermogram contained a single meltevent (189° C.) as shown in FIG. 495 (non-ionized Tabernanthalog (m.p.149° C.) and toluene sulfonic acid (m.p. 105 to 107° C.)), and TGAthermogram exhibited a small weight-loss transition, attributed to waterfrom hydrated tosic acid (FIG. 496 ).

The tabernanthalog benzoate salt (2-R2 (Experiment Reference 2-SampleReference R2), FIGS. 388, 483-486 (B) and 486(C)-486(K) and Table 218)was unique by XRPD (FIG. 404 ) and highly crystalline with lowbackground. Negligible change in the impurity burden was observed inaryl and aliphatic regions (FIG. 484 ). Sharp melt event (onset 183° C.,as shown in FIG. 485 was observed by DSC (non-ionized Tabernanthalog(m.p. 149° C.) and benzoic acid (m.p. 122° C.)), and a flat baseline byTGA analysis (FIG. 486 ).

The salt forms selected for the 1 g scale-up and physicochemicalevaluation (Experiment 3 and the Physicochemical Evaluation study) werethe tabernanthalog tartrate salt, the tabernanthalog benzoate salt andthe tabernanthalog sorbate salt.

iii. Scale-Up Preparation of Nominated Salt Forms (Experiment 3)

The experimental procedure is provided in Section G.ii, and theanalytical characterization data are provided in Iii.

Tabernanthalog (native) was used for the selected salts scale-up.

The tabernanthalog tartrate salt (3-A1; Experiment Reference 3-SampleReference A1), was delivered as a beige solid at 95% uncorr. yield andthe form matched the form, from the previous batch (2-I2; ExperimentReference 2-Sample Reference 12) as shown in FIG. 405 ).

The tabernanthalog benzoate salt (3-B1; Experiment Reference 3-SampleReference B1), was provided as a light brown solid at 87% uncorr. yieldand was the same form as the previous batch (2-R2; Experiment Reference2-Sample Reference R2) as shown in FIG. 406 ).

The tabernanthalog sorbate salt (3-C1; Experiment Reference 3-SampleReference C1), was obtained as a light brown solid at 87% uncorr. yieldand the form matched the form, from the previous batch (2-V2 (ExperimentReference 2-Sample Reference V2) shown in FIG. 407 .

Comparison of m.p. onset and melt enthalpies is summarized in Table 200.Discrepancies in m.p. were evident on the scaled-up samples. A DSCspecimen of 3-B1 (Experiment Reference 3-Sample Reference B1) wasfurther examined because decomposition and ablative activity appeared tooccur well after melting (arrow in FIG. 408 ), the DSC was programmed asfollows: 20° C. to 220° C., 220° C. to 20° C. and 20° C. to 300° C. Theaim was to melt, crystallize and re-melt and assess the new onsettemperature.

The thermocycle applied did not show a crystallization event and a meltwas not observed, therefore this was not repeated on the rest of thespecimens as shown in FIG. 554 .

TABLE 200 Comparison of m.p. onset and melt enthalpies ExperimentReference- Sample pK_(a) 1 pK_(a) 2 DSC (m.p. onset and ReferenceCounter ion pK_(a) 1 pK_(a) 2 enthalpy data) 2-I2 (+)-L-Tartaric acid3.00 4.40 208.22° C. (−137.23 Jg{circumflex over ( )}-1) 3-A1 202.62° C.(−161.53 Jg{circumflex over ( )}-1) 2-R2 Benzoic acid 4.20 N/A 183.18°C. (−157.08 Jg{circumflex over ( )}-1) 3-B1 186.01° C. (−107.08Jg{circumflex over ( )}-1) 2-V2 Sorbic acid 4.75 N/A 143.89° C. (−84.09Jg{circumflex over ( )}-1) 3-C1 146.48° C. (−65.05 Jg{circumflex over( )}-1)

Scale Up of the Tabernanthalog Sorbate Salt to 5 g (Experiment 4)

The experimental procedure is provided in Section G.ii, and theanalytical characterization data is provided in FIGS. 561-572 and Table233.

The salification was performed via heat-up cool-down crystallization oftabernanthalog (native) with sorbic acid from ethanol and afforded lightbrown crystals, (5.1 g, 87% th.) The product was analyzed by XRPD, ¹HNMR, TGA, DSC, HPLC, KF (0.12% w/w water content) and PLM.

In summary, the scale-up of the tabernanthalog sorbate salt (4-A2;Experiment Reference 4-Sample Reference A2), performed as expected asshown in the overlays with 3-C1 ((Experiment Reference 3-SampleReference C1) which corresponds to the initial scale up of nominatedsalts for physicochemical evaluation) depicted in FIGS. 409-412 .

E. Physicochemical Evaluation

An informal physicochemical evaluation of the tabernanthalogmonofumarate salt (Pattern #6a, Form A, 8-A4 of Example 5 [ExperimentReference 8-Sample Reference A4 of Example 5]), the tabernanthalogtartrate salt (3-A1 [Experiment Reference 3-Sample Reference A1]), thetabernanthalog benzoate salt (3-B1 [Experiment Reference 3-SampleReference B1]), and the tabernanthalog sorbate salt (3-C1 [ExperimentReference 3-Sample Reference C1]) was performed to enable selection ofthe preferred salt form. Once the salt is selected, physicochemicalproperties are further evaluated as part of the DS (drug substance)activities.

i. Solubility Determinations in SIF Buffers (Experiment 5)

The experimental procedure is provided in Section G.ii, and theanalytical characterization data are provided in Liv

The solubility of the tabernanthalog monofumarate salt (Pattern #6a,Form A, 8-A4 of Example 5 [Experiment Reference 8-Sample Reference A4 ofExample 5]), the tabernanthalog tartrate salt (3-A1 [ExperimentReference 3-Sample Reference A1]), the tabernanthalog benzoate salt(3-B1 [Experiment Reference 3-Sample Reference B1]), and thetabernanthalog sorbate salt (3-C1 [Experiment Reference 3-SampleReference C1]) were determined in FaSSIF, FeSSIF and FaSSGF by referenceto the calibration curve of Tabernanthalog (native) (Section G.ii) inconjunction with monitoring the suspended phase for evidence of formchange, hydrate formation or possible disproportionation.

The four salt forms (150 mg) were suspended in the relevant SIF buffer(5.0 ml) to give a concentration of 30 mg/ml (Table 214). Thetemperature was maintained at 37° C. for 24 h. At this concentration (30mg/ml), solutions were formed in all apart from the tabernanthalogbenzoate salt (5-C [Experiment Reference 5-Sample Reference C], 5-G[Experiment Reference 5-Sample Reference G], 5-K [Experiment Reference5-Sample Reference K]) which precipitated in all three SIF buffers asshown in FIG. 413 . The tabernanthalog sorbate salt (5-L [ExperimentReference 5-Sample Reference L]) only remained suspended in FaSSGF. Thesuspensions were sampled at the relevant time points and centrifuged.The centrifuged pellets, obtained at the time points were analysed byXRPD as a wet pellet and dried, for evidence of form change.

Chromatography was performed. The tabernanthalog monofumarate salt(Pattern #6a, Form A, 8-A4 of Example 5 [Experiment Reference 8-SampleReference A4 of Example 5]) and the tabernanthalog tartrate salt (3-A1[Experiment Reference 3-Sample Reference A1]) exhibited solubilities >30mg/ml in all three buffers for the duration of the study. Thetabernanthalog sorbate salt (3-C1 [Experiment Reference 3-SampleReference C1]) exhibited a solubility >30 mg/ml in FaSSIF and FeSSIF(Tables 203 and 204).

FaSSIF Buffer

XRPD analysis of the solid from the benzoate salt (5-C [ExperimentReference 5-Sample Reference C]) at each timepoint (as a wet and drypellet) in FaSSIF, confirmed that the phase was consistent with thetabernanthalog benzoate salt (3-B1 [Experiment Reference 3-SampleReference B1]), indicating that the salt was stable and did notdisproportionate in FaSSIF (FIG. 414 ). Chemical purity of the wetpellets obtained from the various time points (5-C; Experiment Reference5-Sample Reference C) is exhibited in Table 201, where the decrease inchemical purity is noticeable (ca. 1.22% area decrease).

TABLE 201 Trended HPLC data of the tabernanthalog benzoate salt inFaSSIF Experiment Reference- Area (mAu*) Tabernanthalog Sample forreference 9.80 10.15 10.60 11.40 12.31 12.54 12.65 Reference- CommentsRRT = 1.00 0.86 0.89 0.93 1.00 1.08 1.10 1.11 3-B1 Tabernanthalog ·21551.15 0.02 0.04 0.61 99.23 0.08 0.02 Benzoate 5-C1 t = 1 h in FaSSIF3193.23 0.92 98.67 0.13 0.28 5-C4 t = 3 h in FaSSIF 2243.96 1.04 98.770.20 5-C7 t = 6 h in FaSSIF 3242.56 1.26 98.58 0.16 5-C10 t = 24 h inFaSSIF 3292.94 1.51 98.01 0.24 0.11 0.13

FeSSIF Buffer

Analogous to the FaSSIF experiment, solid from the benzoate salt (5-G[Experiment Reference 5-Sample Reference G]), was isolated bycentrifugation, analysed at each timepoint as a wet and dry pellet. Thephase was consistent with the tabernanthalog benzoate salt (3-B1[Experiment Reference 3-Sample Reference B1]), indicating that the saltwas stable and did not disproportionate in FeSSIF (FIG. 415 ). TrendedHPLC data of 5-G (Experiment Reference 5-Sample Reference G) showed adecrease in chemical purity like the one observed for 5-C(ExperimentReference 5-Sample Reference C) as shown in Table 202.

TABLE 202 Trended HPLC data of The tabernanthalog benzoate salt inFeSSIF Area Experiment (mAu*) Reference- for Tabernanthalog Samplereference 9.84 10.18 10.64 11.44 12.35 12.58 12.70 Reference CommentsRRT = 1.00 0.86 0.89 0.93 1.00 1.08 1.10 1.11 3-B1 Tabernanthalog ·21551.15 0.02 0.04 0.61 99.23 0.08 0.02 Benzoate 5-G1 t = 1 h in FeSSIF3714.33 0.84 99.05 0.11 5-G4 t = 3 h in FeSSIF 3930.69 0.81 99.03 0.100.06 5-G7 t = 6 h in FeSSIF 4473.57 1.00 98.69 0.15 0.07 0.09 5-G10 t =24 h in FeSSIF 3610.91 0.15 1.36 98.17 0.19 0.13

TABLE 203 Summary of HPLC and XRPD data of the selected Tabernanthalogsalts in SIF buffers at t = 1 h and t = 3 h. Experiment Reference-Weights t =1 h @37° C. t = 3 h @37° C. Sample SIF input Solubility XRPDXRPD Solulibility XRPD XRPD Reference Buffer Input (mg) (mg/ml) (wet)(dried) pH (mg/ml) (wet) (dried) pH 5-A FaSSIF Tabernanthalog• 119.4Solution, N/A N/A 6.37 Solution, N/A N/A 6.55 (pH 6.5) Fumarate >30mg/ml >30 mg/ml 5-B FaSSIF Tabernanthalog• 149.8 Solution, N/A N/A 6.74Solution, N/A N/A 6.46 (pH 6.5) Tartrate >30 mg/ml >30 mg/ml 5-C FaSSIFTabernanthalog• 149.6  8.85 Consistent Consistent 6.63  6.22 ConsistentConsistent 6.32 (pH 6.5) Benzoate with input with input with with inputinput 5-D FaSSIF Tabernanthalog• 150.6 Solution, N/A N/A 6.55 Solution,N/A N/A 6.54 (pH 6.5) Sorbate >30 mg/ml >30 mg/ml 5-E FeSSIFTabernanthalog• 120.2 Solution, N/A N/A 5.08 Solution, N/A N/A 5.07 (pH5.0) Fumarate >30 mg/ml >30 mg/ml 5-F FeSSIF Tabernanthalog• 150.1Solution, N/A N/A 5.01 Solution, N/A N/A 5.03 (pH 5.0) Tartrate >30mg/ml >30 mg/ml 5-G FeSSIF Tabernanthalog• 150.2 10.29 ConsistentConsistent 5.07 10.89 Consistent Consistent 5.00 (pH 5.0) Benzoate withinput with input with with input input 5-H FeSSIF Tabernanthalog• 149.627.15 Insufficient Insufficient 5.19 Solution, N/A N/A 5.18 (pH 5.0)Sorbate for analysis for analysis >30 mg/ml 5-I FaSSGF Tabernanthalog•119.4 Solution, N/A N/A 1.68 Solution, N/A N/A 1.61 (pH 1.6)Fumarate >30 mg/ml >30 mg/ml 5-J FaSSGF Tabernanthalog• 149.8 Solution,N/A N/A 1.63 Solution, N/A N/A 1.64 (pH 1.6) Tartrate >30 mg/ml >30mg/ml 5-K FaSSGF Tabernanthalog• 150.2 29.91 Benzoic Benzoic 1.63 26.21Benzoic Benzoic 1.63 (pH 1.6) Benzoate acid acid acid acid 5-L FaSSGFTabernanthalog• 150.4 21.88 Sorbic acid Sorbic acid 1.73 29.84 SorbicSorbic 1.62 (pH 1.6) Sorbate acid acid

TABLE 204 Summary of HPLC and XRPD data of the selected Tabernanthalogsalts in SIF buffers at t = 6 h and t = 24 h. Experiment Reference-Weights t = 6 h @37° C. t = 24 h @37° C. Sample SIF input SolubilityXRPD XRPD Solubility XRPD XRPD Reference Buffer Input (mg) (mg/ml) (wet)(dried) pH (mg/ml) (wet) (dried) pH 5-A FaSSIF Tabernanthalog• 119.4Solution, N/A N/A 6.54 Solution, N/A N/A 6.41 (pH 6.5) Fumarate >30mg/ml >30 mg/ml 5-B FaSSIF Tabernanthalog• 149.8 Solution, N/A N/A 6.37Solution, N/A N/A 6.47 (pH 6.5) Tartrate >30 mg/ml >30 mg/ml 5-C FaSSIFTabernanthalog• 149.6  8.98 Consistent Consistent 6.40  9.12 ConsistentConsistent 6.50 (pH 6.5) Benzoate with with input with with input inputinput 5-D FaSSIF Tabernanthalog• 150.6 Solution, N/A N/A 6.51 Solution,N/A N/A 6.36 (pH 6.5) Sorbate >30 mg/ml >30 mg/ml 5-E FeSSIFTabernanthalog• 120.2 Solution, N/A N/A 5.05 Solution, N/A N/A 5.01 (pH5.0) Fumarate >30 mg/ml >30 mg/ml 5-F FeSSIF Tabernanthalog• 150.1Solution, N/A N/A 5.01 Solution, N/A N/A 4.93 (pH 5.0) Tartrate >30mg/ml >30 mg/ml 5-G FeSSIF Tabernanthalog• 150.2 12.39 ConsistentConsistent 5.03 10.00 Consistent Consistent 4.97 (pH 5.0) Benzoate withwith input with with input input input 5-H FeSSIF Tabernanthalog• 149.6Solution, N/A N/A 5.07 Solution, N/A N/A 5.05 (pH 5.0) Sorbate >30mg/ml >30 mg/ml 5-I FaSSGF Tabernanthalog• 119.4 Solution, N/A N/A 1.62Solution, N/A N/A 1.79 (pH 1.6) Fumarate >30 mg/ml >30 mg/ml 5-J FaSSGFTabernanthalog• 149.8 Solution, N/A N/A 1.56 Solution, N/A N/A 1.74 (pH1.6) Tartrate >30 mg/ml >30 mg/ml 5-K FaSSGF Tabernanthalog• 150.2 30.86Benzoic Benzoic 1.54 30.69 Benzoic Benzoic 1.70 (pH 1.6) Benzoate acidacid acid acid 5-L FaSSGF Tabernanthalog• 150.4 30.27 Sorbic Sorbic 1.5829.90 Sorbic Sorbic 1.78 (pH 1.6) Sorbate acid acid acid acid

FaSSGF Buffer

The powder pattern of the solid residue (5-K12; Experiment Reference5-Sample Reference K12) obtained at all timepoints did not match thetabernanthalog benzoate salt (3-B1 [Experiment Reference 3-SampleReference B1]), or tabernanthalog (native) (FIG. 416 ).

The reference pattern for benzoic acid was highly preferred and gavepoor agreement with the isolated solid residue, (5-K12; ExperimentReference 5-Sample Reference K12) (FIG. 417 ).

However, by ¹H NMR analysis (FIG. 418 ) of the dry pellet (5-K12;Experiment Reference 5-Sample Reference K12) was consistent with benzoicacid; therefore, at lower pH, a different form of benzoic acid wasisolated. The chemical purity of 5-K (Experiment Reference 5-SampleReference K) did not decrease as significantly during the 24 h in FaSSGF(Table 205), when compared to the tabernanthalog benzoate salt (3-B1[Experiment Reference 3-Sample Reference B1]) in FaSSIF and FeSSIF.

TABLE 205 Trended HPLC data of the tabernanthalog benzoate salt inFaSSGF Area Experiment (mAu*) Reference- for Tabernanthalog Samplereference 9.83 10.17 10.63 11.43 12.45 12.57 12.68 Reference CommentsRRT = 1.00 0.86 0.89 0.93 1.00 1.09 1.10 1.11 3-B1 Tabernanthalog ·21551.15 0.02 0.04 0.61 99.23 0.08 0.02 Benzoate 5-K1 t = 1 h in FaSSGF5398.87 0.55 99.33 0.07 0.02 0.03 5-K4 t = 3 h in FaSSGF 4731.19 0.5899.34 0.07 5-K7 t = 6 h in FaSSGF 5569.91 0.59 99.33 0.08 5-K10 t = 24 hin FaSSGF 5538.89 0.63 99.29 0.08

The powder diffraction patterns of the tabernanthalog sorbate salt solidresidue (5-L; Experiment Reference 5-Sample Reference L) in FaSSGF, wereconsistent with that of sorbic acid (FIG. 419 and FIG. 420 ), while themass balance of tabernanthalog (native) remained in solution. ¹H NMRanalysis of (5-L12; Experiment Reference 5-Sample Reference L12)supported disproportionation when overlaid with tabernanthalog sorbatesalt (3-C1; [Experiment Reference 3-Sample Reference C1]) (FIG. 421 ).

Trended HPLC data of the tabernanthalog sorbate salt in FaSSGF isprovided in Table 206.

TABLE 206 Trended HPLC data of the tabernanthalog sorbate salt in FaSSGFArea Experiment (mAu*) Reference- for Tabernanthalog Sample reference10.16 10.62 11.42 12.45 12.67 12.79 Reference Comments RRT = 1.00 0.890.93 1.00 1.09 1.11 1.12 3-C1 Tabernanthalog · 25461.25 0.05 0.41 99.410.06 0.02 0.05 Sorbate 5-L1 t = 1 h in FaSSGF 4064.06 0.48 99.52 5-L4 t= 3 h in FaSSGF 5542.85 0.49 99.36 0.07 0.08 5-L7 t = 6 h in FaSSGF5626.46 0.55 99.30 0.08 0.07 5-L10 t = 24 h in 5554.20 0.50 99.33 0.090.08 FaSSGF

ii. Equilibrium Humidity Evaluation

The experimental procedure that accompany this experiment is provided inSection G.ii. Photographs of the vials taken during the study areexhibited in FIGS. 430-432 . The fates of the tabernanthalogmonofumarate salt (Pattern #6a, Form A, 8-A4 of Example 5 [ExperimentReference 8-Sample Reference A4 of Example 5]), the tabernanthalogtartrate salt (3-A1 [Experiment Reference 3-Sample Reference A1]), thetabernanthalog benzoate salt (3-B1 [Experiment Reference 3-SampleReference B1]) and the tabernanthalog sorbate salt (3-C1 [ExperimentReference 3-Sample Reference C1]) absorbents, were determined underconstant equilibrium condition at 75% RH/40° C. for 10 days.

All forms were maintained under constant equilibrium humidity (75% RH).XRPD, DSC, TGA, PLM and ¹H NMR analyses were performed on the absorbentsat t=5 d and t=10 d, to confirm their physical fates and to determinethe extent of residual solvent exchange or sequestration.

The Tabernanthalog Monofumarate Salt (40° C., 75% RH)

The characterization data that accompany this experiment is provided inFIGS. 605-620 and Tables 250−251. The absorbent tabernanthalogmonofumarate salt (Pattern #6a, Form A, 8-A4 of Example 5 [ExperimentReference 8-Sample Reference A4 of Example 5)] was included in the panelas the control. The powder diffraction patterns (6-A1 [ExperimentReference 6-Sample Reference A1], t=5 days and 6-A2 [ExperimentReference 6-Sample Reference A2], t=10 days) resembled the input phase(Pattern #6a, Form A, 8-A4 of Example 5 [Experiment Reference 8-SampleReference A4 of Example 5)], confirming that significant structuralreorganization had not occurred (FIG. 422 ). The NMR spectrum overlayconfirmed that the molecular structure of the API was concordant withthe input (FIG. 426 ). No weight loss transitions were detected attypical water release temperatures by TG analyses (FIGS. 609 and 610 )and the flat baseline, observed by DSC at both time points, wasconsistent with no significant water uptake, under this condition (FIGS.607 and 608 ). HPLC data showed a slight decrease in chemical purityafter 10 days [6-A2 (Experiment Reference 6-Sample Reference A2)] asshown in Table 207.

The Tabernanthalog Tartrate Salt (40° C., 75% RH)

The characterization data that accompany this experiment is provided inFIGS. 621-636 and Tables 252−253.

The tabernanthalog tartrate salt at t=5 days (6-B1 [Experiment Reference6-Sample Reference B1]) and t=10 days (6-B2 [Experiment Reference6-Sample Reference B2]) showed no significant changes to the powderdiffraction pattern by XRPD when compared with the input (3-A1[Experiment Reference 3-Sample Reference A1]) as no peak shift to lowerangle, was observed which sometimes is indicative of moisture absorptionwas observed (FIG. 423 ). The absorbent was concordant with the APImolecular structure and ethanol was not detected by ¹H NMR spectroscopy(FIG. 427 ). The TGA profile of 6-B1 (Experiment Reference 6-SampleReference B1) and 6-B2 (Experiment Reference 6-Sample Reference B2) wasconsistent with the input (3-A1 [Experiment Reference 3-Sample ReferenceA1]) with no significant water absorption (FIGS. 625 and 626 ). DSCanalyses exhibited a flat baseline, as no water release endotherms wereevident (FIGS. 623 and 624 ). HPLC data showed the largest decrease inchemical purity after 10 days compared to the rest of the salts (Table208).

The Tabernanthalog Benzoate Salt (40° C., 75% RH)

The characterization data that accompany this experiment is provided inFIGS. 637-652 and Tables 254−255.

By XRPD, tabernanthalog benzoate salt at t=5 days (6-C1 [ExperimentReference 6-Sample Reference C1]) and t=10 days (6-C2 [ExperimentReference 6-Sample Reference C2]) were consistent with the input 3-B1[Experiment Reference 3-Sample Reference B1]) (FIG. 424 ). ¹H NMRspectroscopy confirmed the molecular structure of the input material,with a small decrease in ethanol content from 0.3% w/w to 0.2% w/w (FIG.428 ). TG analyses did not show any weight loss events attributed towater absorbance (FIGS. 641 and 642 ). The DSC thermograms at the twotime points were also consistent with no significant water uptake (FIGS.639 and 640 ). The chemical purity did not decrease significantly at thecessation of the experiment (Table 209).

The Tabernanthalog Sorbate Salt (40° C., 75% RH)

The characterization data that accompany this experiment is provided inFIGS. 653-668 and Tables 256-257.

The powder diffraction pattern of tabernanthalog sorbate at t=5 days(6-D1 [Experiment Reference 6-Sample Reference D1]) and t=10 days (6-D2[Experiment Reference 6-Sample Reference D2]) matched the diffractogramof the input material 3-C1 [Experiment Reference 3-Sample Reference C1])(FIG. 425 ). The ¹H NMR spectrum obtained showed an ethanol contentdecrease from 0.3% w/w to 0.1% w/w and confirmed that the molecularstructure of the API at both time points was concordant with the input(3-C1 [Experiment Reference 3-Sample Reference C1]) (FIG. 429 ). The TGAprofiles from the two time points did not exhibit any water absorptionevents (FIGS. 657 and 658 ). DSC analysis showed a flat baseline,consistent with the input material (FIGS. 655 and 656 ). Trended HPLCdata confirmed the lowest decrease in chemical purity compared to therest of the salts (Table 210).

TABLE 207 Trended HPLC data of 6-A (Experiment Reference 6-SampleReference A) Experiment Area Reference- (mAu*) Tabernanthalog Sample forreference 7.83 8.93 10.04 10.53 11.02 11.63 11.75 11.99 12.24 ReferenceComments RRT = 1.00 0.64 0.73 0.82 0.86 0.90 0.95 0.96 0.98 1.00 8-A4 ofFumarate salt 5659.39 99.04 Example 5 6-A1 t = 5 d at 75% 8764.06 0.250.01 0.04 0.02 0.03 0.02 0.01 0.02 99.12 RH at 40° C. 6-A2 t = 10 d at75% 8319.38 0.27 0.01 0.16 0.06 0.04 0.07 0.01 0.02 98.71 RH at 40° C.Experiment Reference- Tabernanthalog Sample 13.46 13.59 13.71 14.4414.56 16.16 16.40 16.65 16.89 Reference 1.10 1.11 1.12 1.18 1.19 1.321.34 1.36 1.38 8-A4 of 0.96 Example 5 6-A1 0.02 0.08 0.05 0.01 0.04 0.160.01 0.02 0.07 6-A2 0.02 0.13 0.10 0.01 0.05 0.18 0.01 0.02 0.09

TABLE 208 Trended HPLC data of 6-B (Experiment Reference 6-SampleReference B) Experiment Area Reference- (mAu*) Tabernanthalog Sample forreference 8.03 10.45 10.96 11.08 11.47 11.98 12.10 12.36 ReferenceComments RRT = 1.00 0.63 0.82 0.86 0.87 0.90 0.94 0.95 0.97 3-A1Tartrate salt 8237.15 0.05 0.07 0.02 0.21 0.01 6-B1 t = 5 d at 75%3831.45 0.60 0.04 0.03 0.03 0.02 0.11 0.01 0.02 RH at 40° C. 6-B2 t = 10d at 75% 3526.78 0.60 0.04 0.03 0.03 0.03 0.15 0.03 0.03 RH at 40° C.Experiment Reference- Tabernanthalog Sample 12.74 13.89 14.01 14.1414.91 15.03 17.20 Reference 1.00 1.09 1.10 1.11 1.17 1.18 1.35 3-A199.39 0.11 0.02 0.04 0.01 0.04 0.05 6-B1 98.86 0.11 0.03 0.02 0.03 0.030.04 6-B2 98.82 0.09 0.01 0.01 0.03 0.02 0.03

TABLE 209 Trended HPLC data of 6-C (Experiment Reference 6-SampleReference C) Area Experiment (mAu*) Reference- for Tabernanthalog Samplereference 8.12 9.26 10.40 10.91 11.03 11.54 12.05 12.43 12.68 ReferenceComments RRT = 1.00 0.64 0.73 0.82 0.86 0.87 0.91 0.95 0.98 1.00 3-B1Benzoate salt 10224.04 0.19 0.02 0.22 0.26 0.02 0.51 0.01 98.56 6-C1 t =5 d at 75% 10122.50 0.17 0.28 0.10 0.01 0.54 0.01 98.36 RH at 40° C.16-C2 t = 10 d at 75% 4243.62 0.51 0.25 0.09 0.21 0.03 0.47 0.02 98.17RH at 40° C. Experiment Reference- Tabernanthalog Sample 13.95 14.2014.33 14.96 15.09 15.22 15.85 16.87 Reference 1.10 1.12 1.13 1.18 1.191.20 1.25 1.33 3-B1 0.08 0.03 0.04 0.02 0.05 6-C1 0.08 0.04 0.03 0.010.04 0.05 0.01 0.01 16-C2  0.09 0.03 0.03 0.03 0.05

TABLE 210 Trended HPLC data of 6-D (Experiment Reference 6-SampleReference D) Area Experiment (mAu*) Reference- for Tabernanthalog Samplereference 8.11 10.42 10.94 11.07 11.45 11.97 12.48 12.87 13.90 14.2814.93 15.19 15.57 Reference Comments RRT = 1.00 0.63 0.81 0.85 0.86 0.890.93 0.97 1.00 1.08 1.11 1.16 1.18 1.21 3-C1 Sorbate salt 60353.67 0.040.04 0.04 0.07 99.76 0.01 0.02 0.01 6-D1 t = 5 d at 75% 8531.09 0.280.03 0.01 0.01 0.05 0.01 99.52 0.02 0.03 0.01 0.01 RH at 40° C. 6-D2 t =10 d at 75% 15174.05 0.15 0.02 0.01 0.01 0.01 0.04 0.01 99.70 0.01 0.010.01 0.01 RH at 40° C.

iii. Dynamic Vapour Sorption (DVS)

The tabernanthalog monofumarate salt [Pattern #6a, Form A, 8-A4 ofexample 5 (Experiment Reference 8-Sample Reference A4) of Example 5)]was included as the control. Tabernanthalog monofumarate salt [Pattern#6a, Form A, 8-A4 of example 5 (Experiment Reference 8-Sample ReferenceA4) of Example 5)], the tabernanthalog tartrate salt (3-A1 [ExperimentReference 3-Sample Reference A1]), the tabernanthalog benzoate salt(3-B1 [Experiment Reference 3-Sample Reference B1]) and thetabernanthalog sorbate salt (3-C1 [Experiment Reference 3-SampleReference C1]) were equilibrated at 0% RH for 60 min, prior to DVSanalyses (stepped increment % RH up to 90% RH and stepped decrement % RHdown to 0% RH).

Sorption/Desorption Isotherms

The sorption/desorption isotherms are provided in FIGS. 433-436 .

The tabernanthalog Monofumarate salt

The DVS analyses are provided in FIGS. 669 and 670 and the powderdiffraction analysis is provided in FIG. 671 . The tabernanthalogmonofumarate salt [Pattern #6a, Form A, 8-A4 of example 5 (ExperimentReference 8-Sample Reference A4) of Example 5)] exhibited hygroscopicisotherm, with negligible hysteresis (FIG. 433 ). A small peak shift wasevident in the diffraction pattern acquired after 0 to 90 to 0% RHtreatment, when compared to the diffraction pattern acquired at thebeginning of the cycle; that being said, the diffraction patternsclosely resembled each other (FIG. 671 ), indicating that any structuralchanges that had occurred to the absorbent during DVS treatment wereminimal.

The Tabernanthalog Tartrate Salt

The DVS analyses are provided in FIGS. 471 and 472 and the powderdiffraction analyses are provided in FIGS. 474 and 475 . Thetabernanthalog tartrate salt (3-A1 [Experiment Reference 3-SampleReference A1]) showed a hygroscopic type of isotherm which suggestedreversible water affinity. Negligible hysteresis was observed (FIG. 434). The diffraction patterns pre- and post-treatment (0 to 90 to 0% RH)approximately coincided, indicating that minor structural alterations tothe absorbent that occurred under elevated humidity were reversible.

The Tabernanthalog Benzoate Salt

The DVS analyses are provided in FIGS. 486(A) and 486(B), and the powderdiffraction analyses are provided in FIGS. 486(C) and 486(D). Thetabernanthalog benzoate salt (3-B1 [Experiment Reference 3-SampleReference B1]) appeared to be slightly hygroscopic (red line) isotherm(FIG. 435 ). Again, the diffraction pattern acquired after 0 to 90 to 0%RH treatment exhibited a small peak shift when compared to thediffraction pattern of the input, indicating that any structural changesthat had occurred to the absorbent during DVS treatment were minimal.

The Tabernanthalog Sorbate Salt

The DVS analyses are provided in FIGS. 455 and 456 , and the powderdiffraction analyses are provided in FIGS. 458 and 459 . Thetabernanthalog sorbate salt (4-A2 [Experiment Reference 4-SampleReference A2]) was slightly hygroscopic up to 80% RH (red isotherm, FIG.436 ), hysteresis observed in the 80% to 50% range, during thedesorption cycle. The diffraction patterns pre- and post-treatment (0 to90 to 0% RH) approximately coincided, confirming that minor structuralalterations to the absorbent that occurred under elevated humidity werereversible.

The percent mass change numbers and the curve shape of the DVS isotherm,does not seem to result in developability issues associated with thetabernanthalog sorbate salt (4-A2 [Experiment Reference 4-SampleReference A2]) being hygroscopic.

F. Conclusions

The tabernanthalog sorbate salt was the best candidate amongst the saltsthat were screened and physiochemically evaluated and was thereforenominated for polymorph screening. Focusing on its performance in theadvanced physicochemical screening, the tabernanthalog sorbate saltshowed minimal reduction in CP under 75% RH at 40° C. (6-D [ExperimentReference 6-Sample Reference D] from 99.76% area to 99.70% area). It washighly soluble in the SIF buffers used, apart from FaSSGF (5-L[Experiment Reference 5-Sample Reference L]). The tabernanthalog sorbatesalt (3-C1 [Experiment Reference 3-Sample Reference C1] and 4-A2[Experiment Reference 4-Sample Reference A2]) exhibited much highercrystallographic quality than the tabernanthalog monofumarate salt(Pattern #6a, Form A, 4-A4 [Experiment Reference 4-Sample Reference A4])which is a key physical attribute required in later screening, as itresults in better solvent and impurity rejection on scale-up.Furthermore, sorbic acid is GRAS and is in use as a food additive.

G. Experimental

i. Instrumentation

DSC: A Mettler Toledo DSC 3 instrument was used for the thermal analysisoperating with STARe™ software. The analysis was conducted in 40 μl openaluminum pans, under nitrogen and sample sizes ranged from 1 to 10 mg.Typical analysis method was 20 to 250° C. at 10° C./minute.Alternatively, a Mettler Toledo DSC1 with auto-sampler instrument wasused for the thermal analysis operating with STARe™ software. Theanalysis was conducted in 40 μl open aluminum pans, under nitrogen andsample sizes ranged from 1 to 10 mg. Typical analysis method was 25 to30 0° C. at 10° C./minute.

DVS: The moisture sorption properties of the feed API were analyzed byDVS Intrinsic instrument (Surface Measurement System). Approximately20-50 mg of API was weighed on an aluminum pan and loaded into theinstrument equilibrated at 25° C. The sample was allowed to equilibrateunder dry atmosphere (0% relative humidity) for 60 minutes beforeincreasing the humidity from 0% to 30% at 5% step increment and from 30%to 90% at 10% step increment. A desorption cycle was also applied from90% to 30% (10% step) and from 30% to 0% (5% decrement). A rate ofchange in mass per time unit (dm/dt) of 0.002%/min was set as theequilibrium parameter. Kinetic and isotherm graphs were calculated.

LC-MS: Routine Liquid Chromatography-Mass Spectrometry (LC-MS) data werecollected using the Agilent 1260 Infinity II interfaced with 1260Infinity II DAD HS and Agilent series 1260 Infinity II binary pump. Theinstrument used a single quadrupole InfinityLab MSD. The instrument wascalibrated up to 2000 Da.

LC-MS method parameters:

Inj.vol: 5 μl Detection: UV @ 254 nm Mobile Phase A: Acetonitrile+0.1%TFA/H₂O 95:5 Mobile Phase B: Acetonitrile+0.05% TFA/H₂O 5:95

Time (mins) % A % B 0.0 100 0 1 100 0 10.00 0 100 10.01 100 0 12.00 1000Flow Rate: 1 ml/minColumn temperature: 30° C.Run time 12 minutes.

¹H NMR: ¹H NMR Spectra were acquired using a Bruker 400 MHz spectrometerand data was processed using Topspin. Samples were prepared in DMSO-D₆at typical concentrations of 10 to 20 mg/ml and up to 50 mg/ml for ¹HNMR w/w assay and calibrated to the corresponding non-deuterated solventresidual at 2.50 ppm.

¹H NMR w/w assay: Assays (w/w) of API by ¹H NMR spectroscopy weremeasured using Topspin. Internal standard 2,3,5,6-terachloronitrobenzene(TCNB), (ca. 20 mg, F.W. 260.89) was dissolved in DMSO-D₆ (2.0 ml) andthe ¹H NMR spectrum was acquired using an extended relaxation method.

TGA: A Mettler Toledo TGA 2 instrument was used to measure the weightloss as a function of temperature from 25 to 500° C. The scan rate wastypically 5 or 10° C. per minute. Experiments and analysis were carriedout using the STARe™ software. The analysis was conducted in 100 μl openaluminum pans, under nitrogen and sample sizes ranged from 1 to 10 mg.

XRPD: X-ray powder diffraction (XRPD) analysis was carried out using aBruker D2 Phaser powder diffractometer equipped with a LynxEye detector.The specimens underwent minimum preparation but, if necessary, they werelightly milled in a pestle and mortar before acquisition. The specimenswere located at the center of a silicon sample holder within a 5 mmpocket (ca. 5 to 10 mg). The samples were continuously spun during datacollection and scanned using a step size of 0.02° 2-theta (2θ) betweenthe range of 4° to 40°2-theta or 5° to 60°2-theta. Data was acquiredusing either 3 minute or 10-minute acquisition methods.

Data was processed using Bruker Diffrac.Suite. Relative intensity valuesin peak tables were calculated using the Net. intensity values. FT-IR:FT-IR Spectra were acquired using a PerkinElmer Frontier FT-IRspectrometer. Samples were analyzed directly using a universal ATRattachment in the Mid and Far frequency ranges; 4000 to 30 cm¹.Spectrums were processed using Spectrum software. Standard KBr windowsare used for mid-IR applications; polyethylene and polyethylene/diamondwindows are used for operation in the far-IR. Further capabilities ofthe instrument include a liquid flow cell with ZnSe windows used forrapid monitoring of reactions. This couples with Timebase software whichallows time-resolved measurements to be taken.

HPLC (MET/CR/2616): HPLC data was acquired using an Agilent HPLCinstrument. Samples were diluted to 1 mg/mL concentration in H₂O/DMSO(1/1, v/v).

Method Parameters: Column: Halo C18, 150×4.6 mm, 2.7 μm

Inj. volume: 5 μL

Detection: UV @ 212 nm

Mobile Phase A: 0.1% TFA in water/acetonitrile 95/5 v/vMobile Phase B: 0.05% TFA in water/acetonitrile 5/95 v/v

Time % A % B 0.0 100 0 2.0 100 0 25.0 50 50 30.0 0 100 32.0 0 100 32.1100 0 37.0 100 0Flow rate: 1 mL/minColumn temperature: 30° C.Run time: 37 minutesIntegration time: 32 minutesWash vial or syringe wash: Sample diluent

ii. Procedures

Targeted solubility assessment (Experiment Reference 7)

To portions of tabernanthalog (native) (50 mg, 1 wt), were added 5 volaliquots of the relevant solvent (Table 198). Observations were made at20° C., 40° C. and reflux and the mixtures were cooled to 20° C.Contingent upon these findings, an additional 5 vol aliquot of therelevant solvent was added and the process was repeated until 20 vol ofsolvent was added in total.

Heat-up cool-down crystallization salt screen (Experiment 2)

Tabernanthalog (native) (50 mg, 1 wt) was charged to a solution of therelevant counter ion (1.0 mol equivalence of counter ion) in ethanol(5.0 vol, 250 μl). The mixtures were warmed to 85° C. and small aliquotsof water were added until dissolution occurred (Table 212 for additionalcharges of solvent). The solutions were cooled and allowed to standundisturbed under sub-ambient conditions overnight (Table 211).Solutions were observed in all vials upon cooling at 20° C. Productswere isolated via centrifugation. The corresponding pellets weresub-sampled and analyzed wet by XRPD; after which, they were dried at40° C. under reduced pressure over 20 h and reanalyzed by XRPD. Anyproduct that exhibited a unique diffraction pattern was further analyzedby ¹H NMR for confirmation of chemical identity, counter-ionstoichiometry and solvent content and DSC and TGA to record theirthermal profiles. Once the crystallization experiments were completed,salt formation was confirmed by ¹H NMR, XRPD, DSC and TGA.

TABLE 211 Vials that showed crystals upon cooling. ExperimentObservations upon Reference- Taber- Observations sub-ambient InputSample nanthalog upon cooling cooling reference Reference native Counterion pK_(a)1 pK_(a)2 pK_(a)3 to 20° C. to 6 to 8 C. (40 hr)Tabernanthalog 2 - A1 50.30 Hydrobromic acid −9.00 Solution Solutionnative 2 - B1 50.30 Hydrochloric acid −6.00 Solution Solution 2 - C150.20 Sulfuric acid −3.00 1.90 Solution Crystallised 2 - D1 50.50Ethanesulfonic acid −2.10 −1.50 Solution Solution 2 - E1 50.10p-Toluenesulfonic acid −1.30 Solution Crystallised 2 - F1 50.00Methanesulfonic acid 2.10 Solution Solution 2 - G1 50.00 Maleic acid1.90 6.20 Solution Crystallised 2 - H1 50.60 Phosphoric acid 1.90 7.1012.30 Solution Crystallised 2 - I1 50.50 (+)-L-Tartaric acid 3.00 4.40Solution Crystallised 2 - J1 50.80 Ethane-1,2-disulfonic −2.10 −1.50Solution Crystallised acid 2 -K1 50.30 Galactaric acid (mucic 3.10 3.60Solution Crystallised acid) 2 - L1 50.20 Citric acid 3.10 4.80 6.40Solid Crystallised (monohydrate) 2 - M1 50.30 D-Glucuronic acid 3.20Solution Crystallised 2 - N1 50.20 Glycolic acid 3.30 SolutionCrystallised 2 - O1 50.00 (−)-L-Malic acid 3.50 5.10 SolutionCrystallised 2 - P1 50.80 D-Gluconic acid 3.80 Solution Solution 2 - Q150.70 L-Ascorbic acid 4.20 Solution Gum 2 - R1 50.90 Benzoic acid 4.20Solution Crystallised 2 - S1 50.10 Succinic acid 4.20 SolutionCrystallised 2 -T1 50.30 L-Lactic acid 3.90 Solution Solution 2 - U150.70 Adipic acid 4.41 5.41 Solution Solution 2 - V1 50.40 Sorbic acid4.75 Solution Crystallised 2 - W1 50.70 Acetic acid 4.75 SolutionSolution

TABLE 212 Additional volume of solvents charged to achieve fulldissolution at temperature Water Experiment Additional charge forReference- EtOH dissolution Sample EtOH charge charge 0.25 at 70° C.Reference (5 vol, μl) ml + (μl) (μl) 2-A1 250.0 — — 2-B1 250.0 — — 2-C1250.0 —  20 2-D1 250.0 — — 2-E1 250.0 310.0 — 2-F1 250.0 — — 2-G1 250.0— — 2-H1 250.0 310.0 — 2-I1 250.0 310.0 360 2-J1 250.0 — — 2-K1 250.0270.0 720 2-L1 250.0 100.0 — 2-M1 250.0 310.0 150 2-N1 250.0 — — 2-O1250.0 170.0  30 2-P1 250.0 — — 2-Q1 250.0 240.0  20 2-R1 250.0 170.0  702-S1 250.0 170.0  30 2-T1 250.0 — — 2-U1 250.0 — — 2-V1 250.0 — — 2-W1250.0 — —

Scale-Up Preparation of Nominated Salt Forms (Experiment 3)

The tabernanthalog tartrate salt: Tabernanthalog (native) (1.0 g, 1.0wt,) and L-tartaric acid (717.0 mg, 0.72 wt, 1.1 equiv) were dissolvedin ethanol (5.0 ml, 5 vol) and water (5.75 ml, 5.75 vol) at 85 to 90° C.The clear brown solution was left to cool down to ambient (solid wasobserved) before standing undisturbed under 0 to 8° C. conditions for ca18 h. The product was isolated by filtration, de-liquored and left topull dry under steady nitrogen flux for ca. 3 h. No wash cycle wasapplied (to minimize potential losses). The product was off-loaded fromthe filtration assembly and was oven-dried under vacuum at 40° C. for ca18 h to afford 3-A1 (Experiment Reference 3-Sample Reference A1) (1.57g, 95% uncorr. yield). 3-A1 was analyzed by XRPD, ¹H NMR, TGA, DSC,HPLC.

The tabernanthalog benzoate salt: Tabernanthalog (native) (1.0 g, 1.0wt) and benzoic acid (587 mg, 0.59 wt, 1.1 equiv) were dissolved inethanol (5.0 ml, 5.0 vol) and water (850 l, 0.85 vol) at 85 to 90° C.The clear brown solution was left to cool down to ambient (solid wasobserved) before standing undisturbed under sub-ambient conditions forca. 18 h. The product was isolated by filtration, de-liquored and leftto pull dry under steady nitrogen flux for ca. 3 h. No wash cycle wasapplied (to minimize potential losses). The product was off-loaded fromthe filtration assembly and was oven-dried under vacuum at 40° C. forca. 18 h to afford 3-B1 (Experiment Reference 3-Sample Reference B1)(1.34 g, 87% uncorr. yield). 3-B1 was analyzed by XRPD, ¹H NMR, TGA,DSC, HPLC.

The tabernanthalog sorbate salt: Tabernanthalog (native) (1.0 g, 1.0 wt)and sorbic acid (539 mg, 0.54 wt, 1.1 equiv) were dissolved in ethanol(3.0 ml, 3.0 vol) at 85 to 90° C. The clear brown solution was left tocool down to ambient (solid was observed) before standing undisturbedunder sub-ambient conditions for ca 18 h. The product was isolated byfiltration, de-liquored and left to pull dry under steady nitrogen fluxfor ca. 3 h. No wash cycle was applied. The product was off-loaded fromthe filtration assembly and was oven-dried under vacuum at 40° C. for ca18 h to afford 3-C1 (Experiment Reference 3-Sample Reference C1) (1.57g, 87% uncorr. yield). 3-C1 was analyzed by XRPD, ¹H NMR, TGA, DSC,HPLC.

Scale Up of the Tabernanthalog Sorbate Salt to 5 g (Experiment 4)

Tabernanthalog (native) (3.87 g, 1.0 wt) and sorbic acid (2.07 g, 0.53wt, 1.1 equiv) were dissolved in ethanol (11 ml, 3.0 vol) at 85 to 90°C. The clear brown solution was left to cool down to ambient (solid wasobserved) before standing undisturbed under sub-ambient conditions forca 18 h. The product was isolated by filtration, de-liquored and left topull dry under steady nitrogen flux for ca. 3 h. No wash cycle wasapplied. The product was off-loaded from the filtration assembly and wasoven-dried under vacuum at 40° C. for ca 18 h to afford 4-A2 (ExperimentReference 4-Sample Reference A2) (5.05 g, 87% uncorr. yield). 4-A2 wasanalyzed by XRPD, ¹H NMR, TGA, DSC, HPLC.

Calibration Curve of Non-Ionized Tabernanthalog (Experiment Reference 8)

Separate portions of Tabernanthalog (native) were weighed out intoaluminum boats and were charged to the relevant volumetric flasks.Solutions were made to volume with 1 to 1 (v/v) DMSO/purified water togive calibrants of known API concentrations (Table 213) and analyzed byHPLC, suitable to determine the concentration of Tabernanthalog (native)in the SIF buffer solubility study (Experiment 5 and FIGS. 589-604 ).Peak areas of the calibrants were plotted against concentration togenerate the corresponding calibration curve with slope 27622 and R²0.9917 (FIG. 437 ). At the calculated concentrations the measured valueexhibited positive agreement with the predicted value.

It is noted that tabernanthalog is insoluble in typical HPLC samplediluents, acetonitrile/water. Therefore, DMSO and water wereinvestigated as sample diluents. The ratios trialled were DMSO/water(2/3, v/v) and DMSO/water (1/1, v/v), to verify that Tabernanthalog didnot elute in the void, when higher DMSO concentrations were applied.

Thus, DMSO/water (1/1, v/v) was selected as the appropriate diluentcomposition to perform the study and generate the calibration curve, forthe SIF panel solubility.

TABLE 213 Summary of the average peak areas (mAu*s) of the peak areascorresponding to the concentrations used. Experiment Measured Reference-Input Tabernanthalog Volumes of Concentration peak areas x Peak Sampleweight input weights sample tabernanthalog of calibrants areas Referenceaims (mg) diluant (ml) (mg/ml) (mAu*s) (mAu*s) 8-A1 Inj 1 10.00 9.80100.00 0.10 2885.88 2882.36 8-A1 Inj 2 10.00 9.80 100.00 0.10 2878.848-B1 Inj 1 20.00 20.60 100.00 0.21 6010.05 6016.22 8-B1 Inj 2 20.0020.60 100.00 0.21 6022.38 8-C1 Inj 1 30.00 29.30 100.00 0.29 8613.788598.57 8-C1 Ini 2 30.00 29.30 100.00 0.29 8583.36 8-D1 Inj 1 40.0039.90 100.00 0.40 11616.71 11597.46 8-D1 Inj 2 40.00 39.90 100.00 0.4011578.21 8-E1 Inj 1 50.00 50.60 100.00 0.51 14592.63 14593.09 8-E1 Inj 250.00 50.60 100.00 0.51 14593.56 8-F1 Inj 1 60.00 60.20 100.00 0.6017197.63 17169.00 8-F1 Inj 2 60.00 60.20 100.00 0.60 17140.37 8-G1 Inj 170.00 69.00 100.00 0.69 19587.54 19565.97 8-G1 Inj 2 70.00 69.00 100.000.69 19544.40 8-H1 Inj 2 80.00 79.10 100.00 0.79 22049.76 22059.65 8-H1Inj 2 80.00 79.10 100.00 0.79 22069.54 8-I1 Inj 2 90.00 86.00 100.000.86 26032.60 25997.77 8-I1 Inj 2 90.00 86.00 100.00 0.86 25962.94 8-J1Inj 2 100.00 94.10 100.00 0.94 23812.20 23828.71 8-J1 Inj 2 100.00 94.10100.00 0.94 23845.21

Solubility Determinations in SIF Buffers (Experiment 5)

The tabernanthalog monofumarate salt (120 mg; Pattern #6a, Form A; 8-A4of Example 5 [Experiment Reference 8-Sample Reference A4 of Example 5]),the tabernanthalog tartrate salt (150 mg; 3-A1 [Experiment Reference3-Sample Reference A1]), the tabernanthalog benzoate salt (150 mg; 3-B1[Experiment Reference 3-Sample Reference B1]) and the tabernanthalogsorbate salt (150 mg; 3-C1 [Experiment Reference 3-Sample Reference C1])were suspended in the relevant SIF buffer (5.0 ml, except for thetabernanthalog fumarate salt in which 4 ml was used to deliver 30 mg/mlconcentration) at a concentration of 30 mg/ml (Table 214). Thetemperature was maintained at 37° C. for 24 h.

At this concentration (30 mg/ml), solutions were formed in all but thetabernanthalog benzoate salt (5-C, -G, -K [Experiment Reference 5-SampleReference C, G, K, respectively]) in all three SIF buffers and thetabernanthalog sorbate salt (5-L [Experiment Reference 5-SampleReference L]) in FaSSGF.

The suspension was sampled at the relevant time points and centrifuged.The centrifuged supernatant was sub-sampled and analyzed by HPLC and theconcentration of Tabernanthalog (native) in solution was determined bycomparison with the calibration curve (FIG. 437 ). The centrifugedpellets, obtained at the time points were analyzed by XRPD as a wetpellet and dried, for evidence of form change. The remainder of thesolubility panel remained in solution for the duration of the study.

TABLE 214 Experimental summary of the tabernanthalog salts solubility inSIF buffers Experiment Reference- Input Buffer Sample masses InputCharge Reference (mg) reference Input details mw Buffer (ml) 5-A 119.48-A4 of Tabernanthalog · 346.38 FaSSIF (pH 6.5) 4 Example 5 Fumarate 5-B149.8 3-A1 Tabernanthalog · 380.40 FaSSIF (pH 6.5) 5 Tartrate 5-C 149.63-B1 Tabernanthalog · 352.43 FaSSIF (pH 6.5) 5 Benzoate 5-D 150.6 3-C1Tabernanthalog · 342.44 FaSSIF (pH 6.5) 5 Sorbate 5-E 120.2 8-A4 ofTabernanthalog · 346.38 FeSSIF (pH 5.0) 4 Example 5 Fumarate 5-F 150.13-A1 Tabernanthalog · 380.40 FeSSIF (pH 5.0) 5 Tartrate 5-G 150.2 3-B1Tabernanthalog · 352.43 FeSSIF (pH 5.0) 5 Benzoate 5-H 149.6 3-C1Tabernanthalog · 342.44 FeSSIF (pH 5.0) 5 Sorbate 5-I 119.4 8-A4 ofTabernanthalog · 346.38 FaSSGF (pH 1.6) 4 Example 5 Fumarate 5-J 149.83-A1 Tabernanthalog · 380.40 FaSSGF (pH 1.6) 5 Tartrate 5-K 150.2 3-B1Tabernanthalog · 352.43 FaSSGF (pH 1.6) 5 Benzoate 5-L 150.4 3-C1Tabernanthalog · 342.44 FaSSGF (pH 1.6) 5 Sorbate 5-A to 5-L correspondto “Experiment Reference 5-Sample Reference A” to “Experiment Reference5-Sample Reference L”; 8-A4 of Example 5 is Experiment Reference8-Sample Reference A4 of Example 5. 3-A1 is Experiment Reference3-Sample Reference A1; 3-B1 is Experiment Reference 3-Sample ReferenceB1; and 3-C1 is Experiment Reference 3-Sample Reference C1.

Equilibrimn Humidity Evaluation (Experiment 6)

100 mg portions of Tabernanthalog salts (Table 214 Å) were placed in therelevant open vials. The powders were finely divided and distributedevenly over the base of the vial, such that equal material coverageacross the panel was observed. These samples were then maintained 40° C.under 75% RH. The samples were sub-sampled at intervals of 5 and 10 daysand analyzed by ¹H NMR, HPLC, XRPD, DSC, TGA and PLM, for evidence ofphase change or chemical degradation.

TABLE 214A Summary of salts. Inputs Experimental Experimental referenceinput reference Input (mg) 6-A1 8-A4 of 100.5 (Non-ionised) Example 56-B1 3-A1 100.3 (tartarate salt) 6-C1 3-B1 100.3 (benzoate salt) 6-D13-C1 100.4 (sorbate salt) 6-A1 is Experiment Reference 6-SampleReference A1; 6-B1 is Experiment Reference 6-Sample Reference B1; 6-C1is Experiment Reference 6-Sample Reference C1; 6-D1 is ExperimentReference 6-Sample Reference D1; 3-A1 is Experiment Reference 3-SampleReference A1; 3-B1 is Experiment Reference 3-Sample Reference B1; 3-C1is Experiment Reference 3-Sample Reference C1 and 8-A4 of Example 5 isExperiment Reference 8-Sample Reference A4 of Example 5.

H. Characterisation Data

i. Tabernanthalog (Native)

The characterization data of tabernanthalog native are provided in FIGS.393, 438-440, and 442-450 and Table 215.

TABLE 215 XRDP Peak angle data of Tabernanthalog (native). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 10.4 8.47  19 15.1 5.87  2418.9 4.69 100 27.3 3.26  29 27.4 3.26  25

ii. The Tabernanthalog Sorbate Salt (2-V2 (Experiment Reference 2-SampleReference V2), 3-C1 (Experiment Reference 3-Sample Reference C1), 4-A2(Experiment Reference 4-Sample Reference A2))

The representative experiments that results in tabernanthalog sorbatesalt are (2-V2 (Experiment Reference 2-Sample Reference V2), 3-C1(Experiment Reference 3-Sample Reference C1), and 4-A2 (ExperimentReference 4-Sample Reference A2)).

The characterization data of the tabernanthalog sorbate salt areprovided in FIGS. 451-466 and Table 216.

TABLE 216 XRPD Signal angle data of the tabernanthalog sorbate salt(2-V2 (Experiment Reference 2-Sample Reference V2)). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%)  5.7 15.59 100 10.5  8.44  2211.4  7.76  46 17.9  4.95  13 18.8  4.71  32 19.1  4.64  14 21.4  4.16 14 22.6  3.93  22 22.9  3.89  11 24.4  3.65  22 24.7  3.61  41 26.9 3.32  16

iii. The Tabernanthalog Tartrate Salt (2-I2 (Experiment Reference2-Sample Reference I2), 3-A1 (Experiment Reference 3-Sample ReferenceA1))

The representative experiments that results in tabernanthalog tartratesalt are (2-I2 (Experiment Reference 2-Sample Reference 12), and 3-A1(Experiment Reference 3-Sample Reference A1)). The characterization dataof the tabernanthalog tartrate salt are provided in FIGS. 385, 467-472,and 474-482 and Table 217.

TABLE 217 XRPD Signal angle data of the tabernanthalog tartrate salt(2-I2 (Experiment Reference 2-Sample Reference I2)). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 16.1 5.51  22 16.4 5.39  4617.3 5.11 100 18.2 4.87  10 19.9 4.46  32 20.4 4.34  80 21.3 4.16  6222.4 3.97  61 24.0 3.70  32 24.3 3.66  15 26.1 3.41  27 26.8 3.32  1128.3 3.15  37 32.6 2.74  11 32.9 2.72  12 34.3 2.61  13 37.8 2.38  2238.1 2.36  12

IV. The Tabernanthalog Benzoate Salt (2-R2 (Experiment Reference2-Sample Reference R2), 3-1B1 (Experiment Reference 3-Sample Reference1B1))

The representative experiments that results in tabernanthalog benzoatesalt are 2-R2 (Experiment Reference 2-Sample Reference R2), and 3-B1(Experiment Reference 3-Sample Reference B1). The characterization dataof the tabernanthalog benzoate salt are provided in FIGS. 483-486 (K)and Table 218.

TABLE 218 XRPD Signal angle data of the tabernanthalog benzoate salt(2-R2; Experiment Reference 2-Sample Reference R2). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%)  9.0 9.85 100 14.1 6.26  1115.6 5.66  28 16.7 5.31  31 17.7 5.01  19 18.1 4.91  82 19.6 4.52  1921.3 4.16  13 22.9 3.88  15 23.7 3.76  63 24.4 3.64  14 26.3 3.38  3528.9 3.09  29

v. The Tabernanthalog Malate Salt (2-02 (Experiment Reference 2-SampleReference O2))

The characterization data of the tabernanthalog malate salt are providedin FIGS. 488-492 and Table 219.

TABLE 219 XRPD Signal angle data of the tabernanthalog malate salt (2-O2(Experiment Reference 2-Sample Reference O2)). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. 2-θ (º)d Value Rel. Intensity (%)  6.1 14.59  11 14.0  6.31  43 16.7  5.30  4418.3  4.85  29 19.0  4.67  11 19.5  4.56 100 21.4  4.14  55 21.4  4.14 55 23.9  3.71  12 25.1  3.55  17 25.9  3.44  11 27.0  3.30  39 31.2 2.87  12

vi. The tabernanthalog tosylate salt (2-E2 (Experiment Reference2-Sample Reference E2))

The characterization data of the tabernanthalog tosylate salt areprovided in FIGS. 493-496A and Table 220.

TABLE 220 XRPD Signal angle data of the tabernanthalog tosylate salt(2-E2; Experiment Reference 2-Sample Reference E2). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%)  5.5 16.11 100 11.0  8.05  15

vii. The Tabernanthalog Adipate Salt (2-U2; Experiment Reference2-Sample Reference U2)

The characterization data of the tabernanthalog adipate salt areprovided in FIGS. 389 and 509-512 and Table 221.

TABLE 221 XRPD Signal angle data of the tabernanthalog adipate salt(2-U2; Experiment Reference 2-Sample Reference U2). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%)  5.9 15.05  16 12.0  7.39  1715.7  5.62  66 16.5  5.37  49 17.8  4.99 100 18.6  4.76  22 19.4  4.57 76 20.6  4.30  86 21.0  4.24  61 21.4  4.15  20 21.8  4.08  25 24.0 3.71  49 24.6  3.62  20 25.5  3.49  28 25.9  3.44  14 28.2  3.16  1729.9  2.99  14

viii. The Tabernanthalog Glucuronate Salt (2-M2; Experiment Reference2-Sample Reference M2))

The characterization data of the tabernanthalog glucuronate salt areprovided in FIGS. 390 and 514-517 and Table 222.

TABLE 222 XRPD Signal angle data of the tabernanthalog glucuronate salt(2-M2; Experiment Reference 2-Sample Reference M2). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%)  6.6 13.37  92 12.5  7.09  8013.3  6.67  26 15.1  5.87  32 15.4  5.74  13 16.1  5.49  16 18.1  4.89 63 18.7  4.75  42 20.1  4.42  98 20.7  4.29 100 21.4  4.16  27 21.5 4.13  17 22.9  3.88  60 24.5  3.63  62 24.8  3.59  18 25.1  3.55  1725.5  3.48  11 26.5  3.36  28 28.3  3.15  26 28.5  3.13  21 29.9  2.99 31 31.2  2.87  15 32.0  2.79  11 33.5  2.67  16 33.6  2.67  19 34.4 2.61  17 37.8  2.38  10

ix. The Tabernanthalog Phosphate Salt (2-H2; Experiment Reference2-Sample Reference H2)

The characterization data of the tabernanthalog phosphate salt areprovided in FIGS. 391 and 519-522 and Table 223.

TABLE 223 XRPD Signal angle data of the tabernanthalog phosphate salt(2-H2; Experiment Reference 2-Sample Reference H2). 2-θ (°) d Value Rel.Intensity (%) 5.3 16.73 100 10.5 8.41 16 14.4 6.15 60 14.7 6.02 54 15.25.81 16 15.8 5.61 15 17.2 5.16 14 19.5 4.55 19 19.7 4.51 25 20.2 4.40 5022.7 3.92 33 22.9 3.88 37 23.6 3.77 13 24.0 3.71 37 24.3 3.66 20 25.63.47 20 25.5 3.49 31 26.3 3.39 12 29.9 2.98 13 30.1 2.97 10 Reportedonly peaks >10%. Rel. Intensity values calculated based on Net.Intensity values.

x. The Tabernanthalog Edisylate Salt (2-J2; Experiment Reference2-Sample Reference J2)

The characterization data of the tabernanthalog edisylate salt areprovided in FIGS. 392 and 524-527 and Table 224.

TABLE 224 XRPD Signal angle data of the tabernanthalog edisylate salt(2-J2; Experiment Reference 2-Sample Reference J2). 2-θ (°) d Value Rel.Intensity (%) 4.4 20.14 21 4.5 19.50 25 8.1 10.88 22 8.7 10.16 11 12.27.22 16 12.6 7.02 32 12.8 6.91 27 14.0 6.33 20 14.7 6.01 24 15.1 5.87 2116.2 5.47 19 16.8 5.29 21 17.4 5.09 100 18.0 4.93 16 18.4 4.83 27 18.74.75 10 19.9 4.46 80 19.6 4.52 25 19.9 4.45 91 20.4 4.34 30 20.8 4.26 4221.5 4.13 22 21.8 4.07 38 22.2 4.00 18 23.3 3.81 21 24.2 3.68 17 24.53.64 23 25.4 3.50 14 26.8 3.33 17 27.4 3.25 15 28.2 3.16 11 29.2 3.06 15Reported only peaks >10%. Rel. Intensity values calculated based on Net.Intensity values.

I. Experimental Data

i. Heat-Up Cool-Down Crystallization Salt Screen (Experiment 2 RejectedSalt Forms)

The experimental data of the heat-up cool-down crystallization saltscreen (Experiment 2 rejected salt forms) are provided in FIGS. 529-544and tables 225-229.

TABLE 225 XRPD Signal angle data of the tabernanthalog maleate salt(2-G2; Experiment Reference 2-Sample Reference G2). 2-θ (°) d Value Rel.Intensity (%) 9.2 9.65 18 10.4 8.47 26 12.6 7.04 28 16.8 5.27 11 18.94.69 26 19.4 4.57 46 20.7 4.29 100 21.0 4.23 19 22.2 4.01 27 25.3 3.5225 25.3 3.52 29 26.8 3.32 58 27.6 3.22 18 27.7 3.21 13 28.3 3.16 15Reported only peaks >10%. Rel. Intensity values calculated based on Net.Intensity values.

TABLE 226 XRPD Signal angle data of the tabernanthalog galactarate salt(2-K2; Experiment Reference 2-Sample Reference K2). 2-θ (°) d Value Rel.Intensity (%) 5.7 15.49 30 12.0 7.40 17 13.0 6.81 10 14.3 6.20 12 17.15.17 12 17.6 5.04 13 18.1 4.88 46 19.6 4.53 100 21.5 4.13 26 22.0 4.0316 24.0 3.71 13 24.5 3.63 15 26.1 3.41 13 26.8 3.33 20 30.7 2.91 68 34.52.60 28 36.8 2.44 18 37.0 2.43 16 37.6 2.39 35 37.7 2.39 65 Reportedonly peaks >10%. Rel. Intensity values calculated based on Net.Intensity values.

TABLE 227 XRPD Signal angle data of the tabernanthalog citrate salt(2-L2; Experiment Reference 2-Sample Reference L2). 2-θ (°) d Value Rel.Intensity (%) 12.5 7.09 81 13.0 6.79 59 16.6 5.35 100 17.7 5.00 38 17.65.02 44 19.1 4.64 20 19.7 4.51 20 20.9 4.25 75 21.9 4.05 46 23.7 3.75 4526.0 3.42 33 26.9 3.32 11 34.7 2.58 11 Reported only peaks >10%. Rel.Intensity values calculated based on Net. Intensity values.

TABLE 228 XRPD Signal angle data of the tabernanthalog glycolate salt(2-N2; Experiment Reference 2-Sample Reference N2)). 2-θ (°) d ValueRel. Intensity (%) 9.1 9.72 62 9.7 9.09 56 11.6 7.60 13 18.0 4.93 9718.3 4.85 27 19.0 4.67 37 19.6 4.53 25 19.8 4.48 25 20.1 4.41 19 23.53.79 100 23.4 3.80 84 24.6 3.61 13 25.2 3.53 11 26.2 3.40 16 26.5 3.3610 29.5 3.02 23 Reported only peaks >10%. Rel. Intensity valuescalculated based on Net. Intensity values.

TABLE 229 XRPD Signal angle data of the tabernanthalog succinate salt(2-S2; Experiment Reference 2-Sample Reference S2). 2-θ (°) d Value Rel.Intensity (%) 7.9 11.21 14 8.3 10.62 100 11.0 8.02 17 15.4 5.75 27 15.75.62 15 16.1 5.51 19 17.2 5.16 69 20.1 4.41 16 21.3 4.18 16 21.3 4.16 1722.2 4.01 43 23.6 3.77 14 24.1 3.69 23 24.7 3.60 57 28.1 3.17 11 28.93.09 13 29.9 2.98 11 Reported only peaks >10%. Rel. Intensity valuescalculated based on Net. Intensity values.

ii. Scale Up of Nominated Salt Forms (Experiment 3)

The experimental data of the scale up of nominated salt forms(Experiment 3) are provided in FIGS. 545-560 and Tables 230-232. HPLC,DVS and PLM data for these batches are reported in Sections H.ii, H.iii,and H.iv.

TABLE 230 XRPD Signal angle data of tabernanthalog tartrate salt (3-A1;Experiment Reference 3-Sample Reference A1). 2-θ (°) d Value Rel.Intensity (%) 6.0 14.63 13 16.1 5.51 21 16.4 5.39 37 17.3 5.12 100 18.24.87 11 19.9 4.46 27 20.4 4.35 63 21.3 4.16 46 22.3 3.98 59 24.0 3.71 2324.3 3.65 12 26.1 3.41 27 28.3 3.16 31 32.9 2.72 11 37.8 2.38 21Reported only peaks >10%. Rel. Intensity values calculated based on Net.Intensity values.

TABLE 231 XRPD Signal angle data of tabernanthalog benzoate salt (3-B1;Experiment Reference 3-Sample Reference B1). 2-θ (°) d Value Rel.Intensity (%) 9.0 9.82 100 18.0 4.91 78 23.8 3.74 45 Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues.

TABLE 232 XRPD Signal angle data of tabernanthalog sorbate salt (3-C1;Experiment Reference 3-Sample Reference C1). 2-θ (°) d Value Rel.Intensity (%) 5.7 15.54 100 11.4 7.76 42 22.6 3.93 10 24.7 3.60 22Reported only peaks >10%. Rel. Intensity values calculated based on Net.Intensity values.

iii. Scale Up of the Tabernanthalog Sorbate Salt to 5 g (Experiment 4)

The experimental data of the scale up of the tabernanthalog sorbate saltto 5 g (Experiment 4) are provided in FIGS. 561-572 and Table 233.

TABLE 233 XRPD Signal angle data of tabernanthalog sorbate (4-A2;Experiment Reference 4-Sample Reference A2). 2-θ (°) d Value Rel.Intensity (%) 5.7 15.53 100 11.4 7.75 40 22.8 3.89 11 Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues.

iv. Solubility Determinations in SIF Buffers (Experiment 5)

The experimental data of the solubility assessment in SIF buffers(Experiment 5) are provided in FIGS. 573-604 and Tables 234-249. Thepowder diffraction patterns reported here are obtained from the drypellets.

TABLE 234 XRPD Signal angle data of tabernanthalog benzoate salt (5-C3;Experiment Reference 5-Sample Reference C3). 2-θ (°) d Value Rel.Intensity (%) 9.0 9.81 27 11.5 7.72 10 14.2 6.24 20 15.7 5.65 26 16.75.29 34 17.7 5.00 16 18.1 4.89 85 19.4 4.56 13 19.7 4.51 16 21.4 4.15 1723.0 3.87 17 23.0 3.86 20 23.7 3.75 100 24.5 3.64 14 26.4 3.38 25 28.93.09 13 Reported only peaks >10%. Rel. Intensity values calculated basedon Net. Intensity values.

TABLE 235 XRPD Signal angle data of tabernanthalog benzoate salt (5-G3;Experiment Reference 5-Sample Reference G3). 2-θ (°) d Value Rel.Intensity (%) 9.0 9.81 25 14.2 6.24 16 15.7 5.65 19 16.8 5.29 27 17.75.00 16 18.1 4.89 63 19.7 4.51 12 21.4 4.15 16 23.0 3.86 15 23.7 3.74100 26.4 3.37 17 28.9 3.09 11 Reported only peaks >10%. Rel. Intensityvalues calculated based on Net. Intensity values.

TABLE 236 XRPD Signal angle data of tabernanthalog benzoate salt 5-K3(Experiment Reference 5-Sample Reference K3). 2-θ (°) d Value Rel.Intensity (%) 8.1 10.94 100 16.2 5.46 31 17.1 5.17 25 23.7 3.75 23 25.83.46 14 27.7 3.22 10 30.1 2.97 10 Reported only peaks >10%. Rel.Intensity values calculated based on Net. Intensity values.

TABLE 237 XRPD Signal angle data of tabernanthalog sorbate salt (5-L3;Experiment Reference 5-Sample Reference L3). 2-θ (°) d Value Rel.Intensity (%) 11.4 7.77 36 12.9 6.84 29 22.8 3.90 100 23.4 3.80 11 24.73.59 31 27.7 3.22 32 Reported only peaks >10%. Rel. Intensity valuescalculated based on Net. Intensity values.

TABLE 238 XRPD Signal angle data of 5-C6 (Experiment Reference 5- SampleReference C6). Reported only peaks >10%. Rel. Intensity valuescalculated based on Net. Intensity values. Rel. d Intensity 2-θ (º)Value (%) 8.9 9.89 17 14.1 6.27 13 15.6 5.67 23 16.7 5.31 25 17.6 5.0213 18.1 4.91 67 19.6 4.53 11 21.3 4.16 17 22.9 3.88 19 23.7 3.76 10024.4 3.65 13 26.3 3.38 22 28.8 3.09 13

TABLE 239 XRPD Signal angle data of tabernanthalog benzoate salt (5-G6(Experiment Reference 5-Sample Reference G6). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 8.9 9.89 16 14.1 6.26 15 15.6 5.67 25 16.75.31 31 17.7 5.02 15 18.1 4.91 70 19.4 4.58 11 19.6 4.52 15 21.3 4.16 1422.9 3.87 23 23.7 3.75 100 24.4 3.64 13 26.3 3.38 22 28.9 3.09 15 31.72.82 12

TABLE 240 XRPD Signal angle data of tabernanthalog benzoate salt (5-K6(Experiment Reference 5-Sample Reference K6). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 8.1 10.96 100 16.2 5.47 29 17.1 5.18 33 23.73.75 26 25.8 3.46 22 27.7 3.22 16 30.0 2.97 12

TABLE 241 XRPD Signal angle data of tabernanthalog sorbate salt (5-L6;(Experiment Reference 5-Sample Reference L6). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 11.4 7.75 50 12.9 6.83 29 22.8 3.90 100 24.83.59 20 27.7 3.21 23

TABLE 242 XRPD Signal angle data of tabernanthalog benzoate salt (5-C9(Experiment Reference 5-Sample Reference C9). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 8.9 9.89 15 14.1 6.27 12 15.6 5.67 20 16.75.32 20 17.6 5.03 13 18.0 4.91 60 19.4 4.57 10 19.6 4.53 12 21.3 4.16 1522.9 3.88 18 23.6 3.76 100 24.4 3.65 11 26.3 3.39 20 28.8 3.10 13

TABLE 243 XRPD Signal angle data of tabernanthalog benzoate salt (5-G9(Experiment Reference 5-Sample Reference G9). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 9.0 9.84 21 11.4 7.73 10 14.2 6.25 15 15.75.66 24 16.7 5.30 28 17.7 5.01 13 18.1 4.90 64 19.4 4.57 11 19.6 4.52 1321.4 4.15 17 23.0 3.87 20 23.7 3.75 100 24.4 3.64 11 26.4 3.38 24 28.93.09 12

TABLE 244 XRPD Signal angle data of tabernanthalog benzoate salt (5-K9(Experiment Reference 5-Sample Reference K9). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 8.1 10.95 100 16.2 5.47 36 17.1 5.17 57 19.04.67 13 23.7 3.75 57 25.8 3.46 48 27.7 3.22 30 30.0 2.97 25

TABLE 245 XRPD Signal angle data of tabernanthalog sorbate salt (5-L9(Experiment Reference 5-Sample Reference L9). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 11.4 7.76 52 12.9 6.84 25 22.8 3.90 100 24.73.60 14 27.7 3.22 17

TABLE 246 XRPD Signal angle data of tabernanthalog benzoate salt (5-C12(Experiment Reference 5-Sample Reference C12). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 9.0 9.81 22 11.5 7.71 11 14.2 6.24 19 15.75.64 34 16.8 5.29 32 17.7 4.99 17 18.1 4.89 79 19.5 4.55 10 19.7 4.51 1321.4 4.15 17 23.0 3.86 21 23.7 3.75 100 24.5 3.64 13 26.4 3.38 23 28.93.08 13

TABLE 247 XRPD Signal angle data of tabernanthalog benzoate salt (5-G12(Experiment Reference 5-Sample Reference G12). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 8.9 9.89 14 14.1 6.27 15 15.6 5.67 24 16.75.31 28 17.7 5.02 14 18.1 4.91 73 19.6 4.53 14 21.3 4.16 17 22.9 3.88 2023.7 3.76 100 24.4 3.65 13 26.3 3.38 26 28.8 3.09 14

TABLE 248 XRPD Signal angle data of tabernanthalog benzoate salt (5-K12(Experiment Reference 5-Sample Reference K12). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 8.1 10.90 100 16.2 5.47 34 17.1 5.17 72 19.04.67 12 23.7 3.75 74 25.7 3.46 46 27.6 3.22 25 30.0 2.98 24

TABLE 249 XRPD Signal angle data of tabernanthalog sorbate salt (5-L12(Experiment Reference 5-Sample Reference L12). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 11.4 7.76 34 12.9 6.84 29 22.7 3.91 100 24.73.60 17 27.7 3.22 19

v. Equilibrium Humidity Evaluation (75% RH/40° C.), (Experiment 6)

The Tabernanthalog Monofumarate Salt:

The experimental data of the tabernanthalog fumarate salt are providedin FIGS. 605-620 and Tables 250-251.

TABLE 250 XRPD Signal angle data of tabernanthalog monofumarate salt(6-A1; (Experiment Reference 6-Sample Reference A1). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. Rel. d Intensity 2-θ (º) Value (%) 12.9 6.83 10 16.5 5.35 9419.5 4.55 89 19.5 4.54 100 20.6 4.30 86 22.1 4.02 21 25.3 3.51 74 26.13.41 32 33.5 2.67 11

TABLE 251 XRPD Signal angle data of tabernanthalog monofumarate salt(6-A2 (Experiment Reference 6-Sample Reference A2). Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. Rel. d Intensity 2-θ (º) Value (%) 13.0 6.82 10 16.6 5.35 9319.6 4.53 100 20.7 4.30 83 22.1 4.02 21 25.3 3.51 75 26.1 3.41 33 33.52.67 12

The Tabernanthalog Tartrate Salt

The experimental data of the tabernanthalog tartrate salt are providedin FIGS. 621-636 and Tables 252-253.

TABLE 252 XRPD Signal angle data of tabernanthalog tartrate salt (6-B1:(Experiment Reference 6-Sample Reference B1). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. Rel. dIntensity 2-θ (º) Value (%) 16.1 5.52 21 16.4 5.39 38 17.1 5.18 15 17.35.11 100 19.9 4.46 30 20.4 4.35 70 21.3 4.16 47 22.4 3.97 64 24.0 3.7127 24.3 3.66 12 26.1 3.41 28 28.3 3.15 35 32.9 2.72 11 37.8 2.38 19

TABLE 253 XRPD Signal angle data of tabernanthalog tartrate salt (6-B2(Experiment Reference 6-Sample Reference B2). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. 2-θ (º)d Value Rel. Intensity (%) 16.2 5.48 25 16.5 5.36 40 17.4 5.09 100 20.04.44 29 20.5 4.33 63 21.4 4.14 48 22.5 3.96 56 24.1 3.69 23 26.2 3.40 2328.4 3.14 30 37.9 2.37 18

The Tabernanthalog Benzoate Salt

The experimental data of the tabernanthalog benzoate salt are providedin FIGS. 637-652 and Tables 254-255.

TABLE 254 XRPD Signal angle data of tabernanthalog benzoate salt (6-C1;Experiment Reference 6-Sample Reference C1). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. 2-θ (º)d Value Rel. Intensity (%)  9.0 9.85 100  9.1 9.75 11 18.0 4.92 73 23.73.75 36 27.1 3.28 10

TABLE 255 XRPD Signal angle data of tabernanthalog benzoate salt (6-C2(Experiment Reference 6-Sample Reference C2). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. 2-θ (º)d Value Rel. Intensity (%)  9.0 9.80 46 16.8 5.28 12 18.1 4.90 22 19.74.51 15 19.7 4.51 15 23.7 3.74 100 24.4 3.64 21 26.4 3.37 40

The Tabernanthalog Sorbate Salt

The experimental data of the tabernanthalog sorbate salt are provided inFIGS. 653-668 and Tables 256-257.

TABLE 256 XRPD Signal angle data of tabernanthalog sorbate salt (6-D1;Experiment Reference 6-Sample Reference D1). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. 2-θ (º)d Value Rel. Intensity (%)  5.7 15.37 100 11.5 7.71 56 18.9 4.69 16 23.03.86 11

TABLE 257 XRPD Signal angle data of tabernanthalog sorbate salt (6-D2(Experiment Reference 6-Sample Reference D2). Reported only peaks >10%.Rel. Intensity values calculated based on Net. Intensity values. 2-θ (º)d Value Rel. Intensity (%)  5.7 15.49 100 11.4 7.74 40 18.9 4.70 15 18.84.71 13 24.6 3.61 11

vi. Dynamic Vapour Sorption (DVS)

The experimental data are provided in FIGS. 669-671 .

Example 9: Synthesis of Tabernanthalog Fumarate

A. Published Literature Method to Synthesize Tabernanthalog FumarateResults in Crystalline Pattern #1

8-Methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole fumaratesalt The methodology detailed in WO 2020/176599 was followed. In thisparticular example, Fumaric acid (408 mg, 3.5 mmol, 0.8 equiv) was addedto a sealed tube containing acetone (20 mL). The solution was carefullyheated until all of the fumaric acid dissolved. After cooling thesolution to rt, a solution of8-Methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole (1.028 g,4.4 mmol, 1.0 equiv) in acetone (5 mL) was added dropwise, and themixture was cooled in the freezer overnight. The solid was filtered,washed with acetone, and dried under reduced pressure to yield the titlecompound (1.055 g, 69%) as a 1:1 salt.

As-received fumarate material (ref. batch: Sample Reference 1) wascharacterized as Pattern #1 (FIG. 672 ).

B. Novel Method to Synthesize Tabernanthalog Fumarate Results in Form a(Pattern #6a)

8-Methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole fumaratesalt (polymorph Form A) The following is a new synthesis methodidentified through polymorph screening to prepare stable crystallinefumarate Form A.

Tabernanthalog fumarate salt (1.0 g, 1.0 wt) was charged to the vesselat 20° C. Purified water (5 ml, 5.0 vol) was charged at 20° C. and thecontents of the vessel were stirred at 20° C. for ca. 10 days. Thesuspension was filtered through a sintered funnel. The vessel was rinsedwith purified water (0.5 ml, 0.5 vol) at 20° C. and this was used totransfer any remaining solids and to wash the filter cake. The productwas dried on the filter at 20° C. under sustained nitrogen flux for ca.20 to 24 h. The dried material was collected and the yield was recorded(560.6 mg, 56% yield) and analyzed.

The XRPD profile of Pattern #6a, Form A is provided is FIG. 673 .

C. Synthesis of Tabernanthalog Fumarate Form a Based on the Novel Method

8-Methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole fumaratesalt (polymorph Form A)

Experimental description:Samples transferred to a Bruker sample holder.A preliminary scan in the 20 range of 5-100° was performed to determinethe extent of thecrystallinity, and the appropriate settings to use for the full scan.Incident optics: Divergence Slit=1.0 mm| Diffracted optics: Ni Kβfilter.2 theta range: 5-70°, step size=0.03°, 1.0 s step^(−1.)

Synthesis:

To a refluxing suspension of fumaric acid (1.29 g, 11.1 mmol) in acetone(25 mL) was added a suspension of8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole (3.20 g,13.9 mmol) in acetone (25 mL). A yellow precipitate immediately formed.The suspension was heated at reflux for 20 min before cooling overnight.The precipitate was filtered, and the filter cake was washed withacetone (50 mL), and dried on a drying tray at 40° C. for 12 h. Thesolid was suspended in deionised water (20 mL) and heated to 50° C.,where it remained a suspension. The suspension was then cooled to rt andstirred for 12 days. The off-white suspension was isolated byfiltration, and the filter cake was washed with deionised water (2×5 mL)and dried overnight on a drying tray at 40° C. to afford the titlecompound, polymorph Form A (2.80 g, 58%) as a pale yellow solid.Retention time 1.095 min; Calculated for [C₁₄H₁₈N₂O]⁺ 231.1; found231.2; ¹H NMR (400 MHz, DMSO-d₆) δ 10.50 (s, 1H), 7.24 (d, J=8.6 Hz,1H), 6.75 (d, J=2.2 Hz, 1H), 6.66-6.51 (m, 3H), 3.73 (s, 3H), 3.02-2.78(m, 8H), 2.55 (s, 3H).

XRPD of tabernanthalog Fumarate sample prepared is provided in FIG. 674, Table 258.

TABLE 258 XRPD Signal angle data of the Tabernanthalog Fumarate (Form A)sample prepared Pos. [º 2θ] d-spacing [Å] Rel. Int. [%] 12.6 7.02 1315.7 5.63 16 16.2 5.48 98 17.3 5.11 13 18.9 4.68 100 19.2 4.61 75 20.24.39 86 21.6 4.11 27 23.6 3.77 9 24.9 3.57 86 25.8 3.45 38 27.8 3.21 2129.2 3.06 9 33.0 2.71 13 33.0 2.71 13 36.2 2.48 10 37.4 2.40 19 39.32.29 12 41.2 2.19 14 43.7 2.07 8

Example 10: Polymorph Screen of Tabernanthalog Sorbate

Abbreviations Å Unit of atomic measurement (0.1 nm) φ_(i) Water activitycoefficient a_(w) Water activity ASD Amorphous solid dispersion ca.circa (Latin: approximately) cf. Confer/conferatur (Latin: to confer, tocompare) ° C. degree Celsius CP Chemical Purity CP-MAS Cross PolarisedMagic Angle Spinning (¹³C NMR solid state technique) Da Dalton DSCDifferential Scanning Calorimetry (measures changes in heat capacity)DTA Differential Thermal Analyses (measures changes in temperature) DVSDynamic Vapour Sorption (used interchangeably with GVS) e.g. Exempligratia (Latin: for example) etc. Et cetera (Latin: ‘and others’ or ‘andso on’) FaSSIF Fasted State Simulated Intestinal Fluid FaSSGF FastedState Simulated Gastric Fluid FeSSIF Fed State Simulated IntestinalFluid FT-IR Fourier Transformed, InfraRed spectroscopy (prefixed mid andfar) g Gram (s) GRAS Generally Recognised As Safe GVS Gravimetric VapourSorption h Hour (s) HPLC High Performance Liquid Chromatography HSM HotStage Microscopy (thermal microscopy) HUCD Heat-up/cool-downcrystallisation i.e. Id Est (Latin: that is) IR InfraRed Spectroscopy JJoule Kelvin Kelvin. SI unit of temperature, used interchangeably with °C. to express increment/decrement of temperature set point change (e.g.,ramp rate on DSC thermogram 10K/min); note K sign not prefixed by degreesign. KF Karl Fischer aquametry (determination of the water content bycoulometric titration) kg Kilogram (s) LOD Loss On Drying mag.magnification mAu milli-Absorption units (chromatographic unit of peakheight) mAu*s milli-Absorption units swept across by second(chromatographic unit of peak area) MET/CR Aptuit chromatography methodreference min Minute (s) mg Milligram (s) ml Millilitre (s); litre (l)is not a capital noun; however, it is sometimes denoted as L (mL) molmole, amount of substance N/A Not Applicable n.a. not analysed n.d. notdetected nm Nanometre (10⁻⁹ m, 10 Å) NMR Nuclear Magnetic Resonance oabon anhydrous basis osfb on solvent free basis oasfb on anhydrous solventfree basis pH −log [H⁺] or pH = −log a_(H) ⁺ (assuming equivalenthydrogen ion activity) pK_(a) −log (K_(a)), acid dissociation constantpl isoelectric point, quoted in unit pH PLM Polarised Light MicroscopyRelRT Relative Retention Time (not be confused RT) REP/ Aptuit report(REP) reference RFA Request For Analysis (Aptuit unique referencenumber) RH Relative Humidity (a_(w) * 100) RT Room Temperature (ambient,typically: 18 to 23° C.) s Second (s) SC-XRD Single Crystal X-Raystructure Determination SMPT Solvent-mediated phase transition STASimultaneous Thermal Analysis (STA = TGA + DTA) t time in seconds,minutes, hour, days etc. (interval specified in parentheses); alias incommon use tonne (t) t Tonne, metric unit of mass (1000 kg; 1 Mg),(compaction force in kg, suffixed in parentheses) T Temperature recordedin degrees Celsius (° C.); alias in common use, SI unit of magnetic fluxdensity, also denoted T MTBE Methyl tert-butyl ether TCNB2,3,5,6-Tetrachloronitrobenzene (C₆HCl₄NO₂, F.W. 260.89 gmol⁻¹) TFETrifluoroethanol (solvent used for solvent drop grinding) TGAThermogravimetric Analysis th. theoretical UV Ultraviolet vol. Volume orrelative volume vs. versus v/v Volume/volume W Watt w/w Weight/weightXRPD X-Ray Powder Diffraction

DEFINITIONS Isostructural Crystals are said to be isostructural if theyhave the same crystal structure but not necessarily the same celldimensions nor the same chemical composition (Kálmán, A., Párkányi, L. &Argay, G. (1993) Acta Cryst. B49, 1039-1049.) Isomorphic two crystallinesolids are isomorphous if both have the same unit-cell dimensions andspace group (source, vide supra). Isomorphic desolvate via solventrelease from an isostructural solvate. Native Refers to an API in itsnative or non-ionised form. Normal light Light oscillating in alldirections perpendicular to the axis to which it travels. Particle sizeExpressed as a volume distribution, the range x10 >PSD< x90 captures thesizes of 80% of the particles. Plane polarised light Light passedthrough a polaroid filter which allows only light oscillating in oneplane to be transmitted. Polymorphism Crystalline solid able to exhibitdifferent crystalline phases. Photomicrograph Imaged captured of a smallobject under magnification through an optical microscope.Pseudopolymorphism Different crystal structure attributed to theincorporation of molecular water or solvent. Solvates Contains amolecule of solvent in the crystal lattice. Thermogram Differentialscanning calorimetry trace: heat flow on y-ordinate (mW), time(minutes)/temperature (° C.) on x-ordinate.

Summary

Tabernanthalog sorbate salt, Form A crystallised as prisms from ethanoland was identified as the stable single polymorphic form, suitable foradvanced phase development. The sorbate salt exhibited modest wateraffinity (ca. 1% w/w) up to 90% RH. Specimens were retrieved post DVSand analysed by XRPD at 0%, 80% and 90% RH and were consistent with FormA, indicating that the water uptake was predominantly, non-bonded;however, small shifts in d-spacings were evident and minimal hysteresisin the RH range between 70% to 80% RH, was observed.

Tabernanthalog sorbate salt crystal structure (Form A) was determinedand the simulated powder pattern at 100 K, fully explained theexperimentally observed powder pattern at 298 K. A hydrate form was alsoidentified (refer to the SC-XRD section).

Tabernanthalog sorbate salt (Form A) was subjected to stability studiesat 40° C., 75% RH (the experimental data are reported in Experiment 6 ofExample 8.) and 20° C., 95% RH and was sampled at t=5 days and t=10days. The analytical data collected from the experiment performed at 40°C., 75% RH showed that Form A was stable as the powder diffractionpatterns matched the diffractogram of the input material, ¹H NMRanalysis confirmed that the molecular structure of the API wasconcordant with the input and thermal data did not exhibit any waterabsorption events.

More importantly, trended HPLC data confirmed the lowest decrease inchemical purity compared to the rest of the salts. The stability studyat 20° C., 95% RH showed that Tabernanthalog sorbate salt (Form A)converted to Form C (Pattern #2) after 5 days in the open vial and after10 days in the double-bagged vial. Thermal analysis suggested that FormC (Pattern #2) was likely to be a weakly crystal-bonded hydrate and DVSdata obtained from 0% to 90% to 0% RH confirmed this statement as Form C(Pattern #2) reverted to Form A on the desorption cycle (0% to 90 RH).The NMR data collected agreed with the molecular structure of the input.

Solubility assessment of Tabernanthalog sorbate salt (Form A) in SIFbuffers was, as part of the physicochemical evaluation of the salt,which showed that it was readily soluble in FaSSIF and FeSSIF during 24h, and only exhibited disproportionation after 24 h in FaSSGF (theexperimental data are reported in Experiment 5 of Example 8). Sorbicacid is a monobasic acid counter ion and therefore cannot undergore-proportionation

In conjunction with Form A, Tabernanthalog sorbate salt presented in 3different forms: Form B (refer to Table 261A). We believe that Form Band Form C are labile, crystal-bonded hydrates; the TG weight losstransitions were under unity and suggested that regions of disorder werepresent in the bulk phases.

A. Introduction

Tabernanthalog sorbate salt was nominated as the preferred salt versionand this section summarises the data collected from the polymorphscreen, that was performed on tabernanthalog sorbate salt.

B. Project Design

The polymorph screen included the following activities:

-   -   Scale-up of tabernanthalog sorbate salt to ca. 5 g.    -   Full characterisation of the scaled-up batch, including Q ¹H        NMR, XRPD, TGA, DSC, PLM and SC-XRD.    -   Qualitative solubility investigation against 22 solvents        (selected from Classes 1 and 2 ICH Q3C (R8) Residual solvents,        20/05/21).    -   Suspension equilibration panels in selected solvents at 20° C.        and 40° C.    -   Heat-up/cool-down crystallisations in selected solvents.    -   Determination of the relative stability of the identified forms        via competitive suspension equilibration; or if not possible,        this was inferred from the outcome of superficial drying        activities.    -   Evaluation of chemical and physical stability of the selected        form at 20° C./95% RH (for 40° C./95% RH, refer to Example 8)    -   DVS, investigations of the stable form and phase analyses of        residues acquired specific % RH set-points.

The objective of the polymorph screen was to identify a stable,anhydrous monotropic polymorph, that was judged suitable for advancedphase development. The preferred form was tabernanthalog sorbate salt(Form A).

C. Results and Discussion

This section details the work plan that was undertaken to examine thepolymorph screen of tabernanthalog sorbate salt.

1. Tables of Characterisation

The characterisation of the tabernanthalog sorbate salt is summarized inTables 259-261.

TABLE 259 Tabernanthalog sorbate salt (Form A). Provenances of referencebatches Tabernanthalog sorbate salt (Form A) Experiment 1- Referencebatches: Experiment 1-Sample A2, Sample A2: Experiment 13-Sample C1,crystallised Experiment 11-Sample A1 from ethanol. Molecular weight:342.44 gmol⁻¹ The product Exact molecular weight: 342.1943 was isolatedby Molecular formula: C₂₀H₂₆N₂O₃ suction filtration Unary/mono sorbate:24.7% w/w th., sorbic acid and dried under (i.e., 1.0 mol of API to 1.0mol sorbic acid). steady nitrogen SCXRD: Unary/mono sorbate. Thesimulated powder flux for ca 3 h; pattern, predicted from single crystalstructure at 100K the filter cake agreed with the experimentallyobserved (5.2 g, 0.2% Form A powder pattern obtained at 298K w/wethanol) (refer to the SC-XRPD section). was off-loaded Nature ofhydrogen bonding: Hydrogen bonding between from the both oxygenmolecules on the sorbate ion. One to N1 filtration (tryptamine nitrogenatom) of one API molecules, apparatus, the other to N2 (hydro-azepinenitrogen atom) of a trayed-up and separate API molecule. Due to hydrogenbonding present dried under in the structure builds up chains betweenAPI and salt reduced molecule. Causing stacking of API and sorbatemolecules pressure at closely packed to one another. This leads to lessfree space 40° C. for ca. in the crystal structure and void radius ofonly ~0.9 A, 18 h. much smaller than the 1.4 required for a watermolecule Experiment 13- to occupy. Sample C1: Bond between Sorbates andAPI, N1—O3, 2.857 Å (hydrogen bond), N2—O2, 2.7015 Å (salificationhydrogen bond) N1 = Indole, N2 = Hydroazepine. Sorbate molecule isdisordered and bond lengths stated are an average of the two mappedpositions. Crystal system 100(2) K: monoclinic Space group 100(2) K:P2₁/c Unit cell 100(2) K: a = 9.3410(3) Å, b = 6.4173(2) Å, c =30.5108(12) Å. A = γ = 90º β = 95.374(3)º, V = 1820.90(11) Å3.Asymmetric unit: contains one API molecule one sorbate ion. XRPD: 5.7°,11.4º, 22.8º (Experiment 1-Sample A2, refer to FIG. 564 and Table 273).DSC: onset 140.03° C. (−106.66 Jg⁻¹, endotherm, melt) (Experiment1-Sample A2, refer to Section D.1). TGA: onset 177.6° C. (−36.4% w/w,ablation) 263.5° C. (−59% w/w, ablation) (Experiment 1-Sample A2, referto Section D.1). DVS 0 to 90 to 0% RH (dm/dt <0.002%): 0.0 (0.00%), 5.0(0.0%), 10.0 (0.01%), 15.0 (0.01%), 20.0 (0.02%), 25.0 (0.03%), 30.0(0.03%), 40.0 (0.05%), 50.0 (0.07%), 60.0 (0.10%), 70.0 (0.14%), 80.0(0.21%), 90.0 (0.98%), 90.0 (0.98%), 80.0 (0.48%), 70.0 (0.30%), 60.0(0.18%), 50.0 (0.06%), 40.0 (0.03%), 30.0 (0.00%), 25.0 (0.00%), 20.0(0.02%), 15.0 (0.03%), 10.0 (0.04%), 5.0 (0.05%), 0.0 (0.06%)(Experiment 1-Sample A2, refer to Section D.1). UV chromatographicpurity: 99.64% area (212 nm), (Experiment 1-Sample A2, refer to sectionD. 1) ¹H NMR: (DMSO-d₆, 400 MHZ); δ 10.5 (s, 1H), 7.2 (d, J = 8.56 Hz,1H), 7.1 (dd, J = 15.2, 15.3 Hz, 1H), 6.7 (d, J =1.9 Hz, 1H), 6.6 (dd, J= 8.56, 2.2 Hz, 1H), 6.2 (d, m, 2H), 5.8 (d, J = 15.0 Hz, 1H), 3.7 (s,3H), 2.8 (m, 2H), 2.7 (m, 6H), 2.4 (s, 3H), 1.8 (d, J = 5.8 Hz, 3H) ppm;conforms to the molecular structure (Σ25H; this event was observed whensample was re-prepared for TGA analysis after 7 days (refer to FIG.564)), (Experiment 1-Sample A2, refer to D.1) Residual solvents ICH Q3C(R8): Experiment 1-Sample A2 (ethanol 0.1% w/w, ICH listed 5000 ppm) Q¹H NMR: 99.9% w/w (Experiment 1-Sample A2, refer to Section D.1)Appearance: refer to section G. 1 (Experiment 13-Sample C1).

TABLE 260 Tabernanthalog sorbate salt (Form B, Pattern #1). Provenancesof reference batches Tabernanthalog sorbate salt (Form B, Pattern #1)Experiment 2- Reference batches: Experiment 2-Sample S1, Sample S1:Experiment 6-Sample A1 and crystallised Experiment 12-Sample A2. fromwater Molecular weight: 342.44 gmol⁻¹ Experiment 6- Exact molecularweight: 342.1943 Sample A1: Molecular formula: C₂₀H₂₆N₂O₃ crystallisedUnary/mono salt: from (i.e., 1.0 mol of API to 1.0 mol sorbic acid).methanol/ XRPD: 7.5º, 15.1º water (Experiment 2-Sample S1, refer toSectionD.2) (2/1, v/v) DSC: onset 48.4° C. via (−231.36 Jg⁻¹, endotherm,dehydration), evaporation 69.9° C. (−160.38 Jg⁻¹, endotherm,dehydration), Experiment 144.6° C. (−102.24 Jg⁻¹, endotherm, melt) 12-(Experiment 6-Sample A1, refer to section D.2). Sample A2: TGA: onset54.8° C. (−1.37% w/w, dehydration; this event was observed when samplewas re-prepared for TGA analysis after 7 days (refer to FIG. 564)164.37° C. (−29.24% w/w, ablation) (Experiment 6-Sample A1, refer tosection D.2) ¹H NMR: (DMSO-d₆, 400 MHz); δ 10.3 (s, 1H), 7.2 (d, J =8.56 Hz, 1H), 7.1 (ddd, J = 15.2, 15.3, 0.56 Hz, 1H), 6.7 (d, J = 2.24Hz, 1H), 6.6 (dd, J = 8.54, 2.33 Hz, 1H), 6.2 (d, m, 2H), 5.8 (d, J =15.32 Hz, 1H), 3.7 (s, 3H), 2.8 (m, 2H), 2.7 (m, 6H), 2.4 (s, 3H), 1.8(d, J = 5.96 Hz, 3H) ppm; conforms to the molecular structure (Σ25H; themolecular formula (C₂₀H₂₆N₂O₃) includes the carboxylic acid protonhowever, it co-resonates with water), (Experiment 6-Sample A1, refer tosection D.2) Residual solvents ICH Q3C (R8): Experiment 6-Sample A1:Methanol not detected Appearance: refer to Section D.2 (Experiment12-Sample A2).

TABLE 261 Tabernanthalog sorbate salt (Form C, Pattern #2). Provenancesof reference batches Tabernanthalog sorbate salt (Form C, Pattern #2)Experiment 3- Reference batches: Experiment 3-Sample R1 and Sample R1:Experiment 10-Sample A2 crystallised Molecular weight: 342.44 gmol⁻¹from water Exact molecular weight: 342.1943 Experiment 10- Molecularformula: C₂₀H₂₆N₂O₃ Sample A2: Unary/mono salt: material from (i.e., 1.0mol of API to 1.0 mol sorbic acid) stability at 95% XRPD: 5.7º, 11.1º,11.5º, 13.9°, 16.7º, 17.3º, 17.8º, 18.5º, RH 18.7º, 20.1º, 22.4º, 29.7º(Experiment 10-Sample A2) (refer to Section D.3) DSC: onset 76.6° C.(−99.32 Jg⁻¹, endotherm), 145.1° C. (−95.88 Jg⁻¹, endotherm) (Experiment10-Sample A2), (refer to section D.3). TGA: onset 71.6° C. (−4.4% w/w,dehydration), 168.7° C. (−27.9% w/w, ablation), (Experiment 10-SampleA2), (refer to section D.3) UV chromatographic purity: 99.69% area (212nm), (Experiment 10-Sample A2), (refer to section D.3) ¹H NMR: (DMSO-d₆,400 MHz); δ 10.3 (s, 1H), 7.2 (d, J = 8.6 Hz, 1 H), 7.1 (ddd, J = 15.3,14.8, 0.56 Hz, 1H), 6.7 (d, J = 2.2 Hz, 1H), 6.6 (dd, J = 10.8, 6.2 Hz,1H), 6.2 (m, 2H), 5.8 (d, J = 15.3 Hz, 1H), 3.7 (s, 3H), 2.9 (m, 2H),2.7 (m, 6H), 2.4 (s, 3H), 1.8 (d, J = 5.9 Hz, 3H) ppm; conforms to themolecular structure (Σ25H; the molecular formula (C₂₀H₂₆N₂O₃) includesthe carboxylic acid proton however, it co-resonates with water),(Experiment 10-Sample A2), (refer to section D.3) Residual solvents ICHQ3C (R8): Experiment 10-Sample A2: Methanol not detected Appearance:refer to section D.3 (Experiment 10-Sample A2 and Experiment 3-SampleR1)

2. Polymorph Screen

The summary of the Forms is provided in Table 261A.

Qualitative Solubility Screen (Experiment Reference: 2)

For experimental procedure refer to Section F.2. The characterizationdata reported here are for Pattern #1 (Form B, Experiment 2-Sample S1,refer to Section D.2), as the rest of the pellets resembled Form A byXRPD (refer to Table 263).

Note: For this experiment a scale up of the Tabernanthalog sorbate saltwas performed. For experimental procedure refer to Section F.6 and forexperimental characterization data refer to Section D.1. The product(Experiment 1-Sample A2, Form A, 5.05 g, 87% uncorr. yield) was analysedby DSC, TGA, ¹H NMR, XRPD, KF (0.12% w/w water content) and PLM. All theanalysis results were congruent with the reference pattern (Experiment13-Sample C1, Form A).

The qualitative solubility screen was carried out to determine the rangeof solvents incorporated into future suspension equilibration panels.Products that crystallised were centrifuged and analysed as wet pelletby XRPD, dried under reduced pressure and re-analysed by XRPD, withselected samples further analysed by TGA and ¹H NMR spectroscopy.

Apart from minor strain effects, the products were consistent with theinput phase (Form A), indicating that the sorbate salt is predominantlymonomorphic (the preferred result); however, a metastable phase wasdetected as wet pellet, from water, this reverted to Form A, when dried(entry-S1), yet contained a low-level transition, by TGA.

Based on the finds from this evaluation, two panels of suspensionequilibration of Tabernanthalog sorbate salt were performed at 20 and40° C. against 22 solvents, including the aqueous systems.

The solubility screen of tabernanthalog sorbate is provided in Table 262and the summary of the results is provided in Table 263.

TABLE 262 Solubility screen of Tabernanthalog sorbate. 5 vol 10 vol 15vol 20 vol Solid Solid Solid Solid ICH Solution at on Solution at onSolution at on Solution at on Reference Solvent Class 20° C. 40° C.reflux cooling 20° C. 40° C. reflux cooling 20° C. 40° C. reflux cooling20° C. 40° C. reflux cooling Experiment 2-Sample -A1 Acetone 3 x x x x x✓ ✓ x x ✓ ✓ x x ✓ ✓ Experiment 2-Sample -B1 MeCN 2 x x ✓ ✓ x x ✓ ✓ x x ✓✓ x x ✓ ✓ Experiment 2-Sample -C1 TBME 3 x x x x x x x x x x x xExperiment 2-Sample -D1 Chlorobenzene 2 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓Experiment 2-Sample -E1 DCM 2 x x ✓ ✓ x ✓ ✓ x ✓ Experiment 2-Sample -F1EtOH 3 x x ✓ ✓ x ✓ ✓ x ✓ Experiment 2-Sample -G1 EtOAc 3 x x ✓ ✓ x x ✓ ✓x x ✓ ✓ x x ✓ ✓ Experiment 2-Sample -H1 Ethyl formate 3 x x ✓ ✓ x x ✓ ✓x x ✓ ✓ x x ✓ ✓ Experiment 2-Sample -I1 Heptane 3 x x x x x OiledExperiment 2-Sample -J1 Isopropyl acetate 3 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x✓ ✓ Experiment 2-Sample -K1 MeOH 2 ✓ x Experiment 2-Sample -L1 Methylacetate 3 x x x x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ Experiment 2-Sample -M1 MEK 3 xx ✓ ✓ x x ✓ ✓ x x ✓ ✓ x ✓ ✓ Experiment 2-Sample -N1 MeTHF # x x ✓ ✓ x x✓ ✓ x x ✓ ✓ x x ✓ ✓ Experiment 2-Sample -O1 Nitromethane 2 x x ✓ ✓ x x ✓✓ x x ✓ ✓ x x ✓ ✓ Experiment 2-Sample - P1 2-Propanol 3 x x ✓ ✓ x x ✓ ✓x x ✓ ✓ x x ✓ ✓ Experiment 2-Sample -Q1 THF 2 x x ✓ ✓ x x ✓ Experiment2-Sample -R1 Toluene 2 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ A1270-048-S1Water # x x ✓ ✓ x x ✓ Experiment 2-Sample -T1 Acetone/Water 2 x ✓ ✓ (5%v/v, 0.5 aw) Experiment 2-Sample-U1 Ethanol/Water 2 ✓ (15% v/v, 0.5 aw AExperiment 2-Sample - Isopropanol/Water 2 x ✓ V1 (12%, v/v, 0.5 aw)Experiment 2- Acetone 3 x x x x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ Sample A1Experiment 2- MeCN 2 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ Sample B1Experiment 2- TBME 3 x x x x x x x x x x x x Sample C1 Experiment 2-Chlorobenzene 2 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ × x ✓ ✓ Sample D1 Experiment 2-DCM 2 x x ✓ ✓ x ✓ ✓ x ✓ Sample E1 Experiment 2- EtOH 3 x x ✓ ✓ x ✓ ✓ x ✓Sample F1 Experiment 2- EtOAc 3 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ SampleG1 Experiment 2- Ethyl formate 3 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ SampleH1 Experiment 2- Heptane 3 x x x x x Oiled Sample I1 Experiment 2-Isopropyl acetate 3 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ Sample J1 Experiment2- MeOH 2 ✓ x Sample K1 Experiment 2- Methyl acetate 3 x x x x x ✓ ✓ x x✓ ✓ x x ✓ ✓ Sample L1 Experiment 2- MEK 3 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x ✓ ✓Sample M1 Experiment 2- MeTHF # x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ SampleN1 Experiment 2- Nitromethane 2 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ SampleO1 Experiment 2- 2-Propanol 3 x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ Sample P1Experiment 2- THF 2 x x ✓ ✓ x x ✓ Sample Q1 Experiment 2- Toluene 2 x x✓ ✓ x x ✓ ✓ x x ✓ ✓ x x ✓ ✓ Sample R1 Experiment 2- Water # x x ✓ ✓ x x✓ Sample S1 Experiment 2- Acetone/Water 2 x ✓ ✓ Sample T1 (5% v/v, 0.5aw) Experiment 2- Ethanol/Water 2 ✓ Sample U1 (15% v/v, 0.5 aw)Experiment 2- Isopropanol/Water 2 x ✓ Sample V1 (12%, v/v, 0.5 aw)

TABLE 263 Summary of results. Assignment Assignment Reference Solvent(wet pellet XRPD) (dry pellet XRPD) ¹H NMR Experiment 2- Acetone Form AForm A — Sample A1 (absent shoulder 22.82º 2θ) Experiment 2- MeCN Form AForm A — Sample B1 (absent shoulder 18.77º, 22.82º 2θ) Experiment 2-TBME Form A Form A insufficient Sample C1 (shoulder 22.60º 2θ) materialExperiment 2- Chlorobenzene Form A Form A — Sample D1 (absent shoulder18.77º 2θ) (shoulder 22.62º 2θ) Experiment 2- DCM Form A + splitreflections 5.90º, Form A — Sample E1 10.70º, 11.62º, 23.14º 2θExperiment 2- EtOH Insufficient material — — Sample F1 Experiment 2-EtOAc Form A Form A — Sample G1 Experiment 2- Ethyl formate Form A + newshoulders Form A + new shoulders insufficient Sample H1 18.72º, 23.01º2θ 18.30º, 19.46º, 23.01º 2θ material Experiment 2- Heptane Oiled — —Sample I1 Experiment 2- Isopropyl Form A, some shift of d-spacings FormA — Sample J1 acetate Experiment 2- MeOH — — — Sample K1 Experiment 2-Methyl acetate Form A Form A — Sample L1 Experiment 2- MEK Form A +shoulder 22.89º 2 Form A + new shoulder MEK n.d. Sample M1 11.61º 2θExperiment 2- MeTHF Form A + split reflections Form A Sample N1 5.87º,11.56º, 2θ Experiment 2- Nitromethane Form A + split reflections Form Anitromethane Sample O1 17.97º, 2θ (strain 23.04º 2θ) n.d. Experiment 2-2-Propanol Form A Form A — Sample P1 Experiment 2- THF Form A + newshoulders Form A — Sample Q1 22.52º 2θ Experiment 2- Toluene Form A FormA — Sample R1 (strain 14.63º, 24.62º 2θ) Experiment 2- Water Pattern #1Converted into Form A insufficient Sample S1 materiall for KF analysisExperiment 2- Acetone/Water Insufficient material — — Sample T1 (5% v/v,0.5 aw) Experiment 2- Ethanol/Water Insufficient material — — Sample U1(15% v/v, 0.5 aw) Experiment 2- Isopropanol/ Insufficient material — —Sample V1 Water (12%, v/v, 0.5 aw) ¹H NMR spectroscopy was performed onselected samples to determine solvent content and confirm the chemicalidentity of the output (refer to FIG. 676, FIG. 677 and FIG. 678). Thestructure did not show any alterations/degradation on the selectedbatches. Solvents were not retained.

Suspension Equilibration at 20 and 40° C. Experiment Reference: 3 and 4

For experimental procedure refer to Section F.2. Suspensionequilibration at 20° C. (A1270-052) delivered Pattern #2 (Form C,Experiment 3-Sample R1) as a new metastable form and thecharacterization data are reported in Section D.3. Suspensionequilibration at 40° C. (A1270-056) gave Pattern #5 (Experiment 4-SampleE1, refer to Section D.6) and Pattern #3 (Experiment 4-Sample H1, referto Section D.4) as new metastable forms. Pattern #4 is reported asexperiment number Experiment 5-Sample R1 (refer to Section D.5).

Suspension equilibration is a thermodynamic dwelling technique, designedto promote the evolution of the API into a more stable phase. Thepurpose of this panel is to determine if Form A evolves into asupra-ordinate form. The companion panel at 40° C. set-point is in placeto detect enantiotropic behaviour via different relative proportions indifferent solvents. XRPD data of the moist pellets obtained from thesuspension equilibration study at 20° C. (Experiment 3, refer to Table264) were consistent with Form A, except from water which was different(refer to FIG. 679 ); however, upon oven drying, the phase reverted toForm A, indicating that Pattern #2 is almost certainly metastable withrespect to Form A. Analyses of the rest of the dried pellets wereconsistent with the stable form (Form A).

TABLE 264 Suspension equilibration at 20° C. Solvent Obser- Obser-Obser- Input (1 part, vations vations vations XRPD XRPD weight 5 vol Keychemical b.p. ICH (t = 0 (t = 1 d (t = 10 d (IPC, (post oven References(mg) total) functional groups (° C.) Classes @ 20° C.) (@ 20° C.) @ 20°C.) 6 d, wet) dried) Experiment 49.6 Acetone Symmetrical ketone 56 3Suspension Suspension Suspension Form A Form A 3-Sample A Experiment50.2 Aceto- Simple dipolar- 82 2 Suspension Suspension Suspension Form AForm A 3-Sample B nitrile aprotic nitrile Experiment 49.7 tBME Branchedaliphatic 55 3 Suspension Suspension Suspension Form A Form A 3-Sample Cmethoxyether Experiment 49.8 Chloro- Aromatic halide 131 2 SuspensionSuspension Suspension Form A Form A 3-Sample D benzene Experiment 49.7Dichloro- Chlorinated 40 2 Suspension Suspension Suspension Form A FormA 3-Sample E methane hydrocarbon Experiment 50.0 Ethanol Linear 78 3Suspension Suspension Suspension Form A Form A 3-Sample F aliphaticalcohol Experiment 50.1 Ethyl Aliphatic ester 75 3 Suspension SuspensionSuspension Form A Form A 3-Sample G acetate Experiment 50.4 EthylAldehyde 54 3 Suspension Suspension Suspension Form A Form A 3-Sample Hformate aliphatic ester Experiment 50.3 Heptane Linear alkane 98 3Suspension Suspension Suspension Form A Form A 3-Sample I Experiment50.1 Isopropyl Branched 87 3 Suspension Suspension Suspension Form AForm A 3-Sample J acetate aliphatic ester Experiment 49.5 MethylAliphatic ester 57 3 Suspension Suspension Suspension Form A Form A3-Sample K Acetate Experiment 50.1 MEK Asymmetric 80 3 SuspensionSuspension Suspension Form A Form A 3-Sample L dialkyl ketone Experiment50.2 2-Methyl Asymmetric 80 # Suspension Suspension Suspension Form AForm A 3-Sample M THF cyclic ether Experiment 49.7 Nitro- Dipolar 100 2Suspension Suspension Suspension Form A Form A 3-Sample N methaneaprotic nitro Experiment 50.0 2- Branched 83 3 Suspension SuspensionSuspension Form A Form A 3-Sample O Propanol aliphatic alcoholExperiment 50.2 Tetra- Symmetric 66 2 Suspension Suspension SuspensionForm A Form A 3-Sample P hydrofuran cyclic ether Experiment 49.9 TolueneAlkyl 111 2 Suspension Suspension Suspension Form A Form A 3-Sample Qaromatic hydrocarbon Experiment 50.3 Water Dihydrogen oxide 100 #Suspension Suspension Suspension Pattern #2 Form A 3-Sample R Experiment50.0 Acetone/ Symmetrical ketone/ 56 3 Solution Solution Feint — —3-Sample S Water Dihydrogen oxide suspension (10% v/v, 0.5 aw)Experiment 50.3 Isopro- Branched 83 3 Solution Solution Solution — —3-Sample T panol/ aliphatic alcohol/ Water Dihydrogen oxide (12%, v/v,0.5 aw)

TABLE 265 Suspension equilibration at 40° C. Solvent XRPD Input (1 part,Observations Observations Observations XRPD (post weight 5 vol Keychemical b.p. ICH (t = 0 (t = 1 d (t = 10 d (IPC, oven References (mg)total) functional groups (° C.) Classes @ 40° C.) @ 40° C.) @ 40° C.) 6d, wet) dried) Experiment 49.7 Acetone Symmetrical ketone 56 3Suspension Suspension Suspension Form A Form A 4-Sample A Experiment49.8 Acetonitrile Simple dipolar- 82 2 Suspension Suspension SuspensionForm A Form A 4-Sample B aprotic nitrile Experiment 49.5tert-Butylmethyl Branched aliphatic 55 3 Suspension SuspensionSuspension Form A Form A 4-Sample C ether methoxyether (disordered)Experiment 49.5 Chlorobenzene Aromatic halide 131 2 SuspensionSuspension Suspension Form A Form A 4-Sample D Experiment 49.8Dichloromethane Chlorinated 40 2 Partial Solution Beige Pattern #5Insuff. 4-Sample E hydrocarbon suspension mat Experiment 50.3 EthanolLinear aliphatic 78 3 Partial Partial Feint Form A Form A 4-Sample Falcohol suspension Experiment 50.2 Ethyl acetate Aliphatic ester 75 3Suspension Suspension Suspension Form A Form A 4-Sample G Experiment50.0 Ethyl formate Aldehyde aliphatic 54 3 Suspension SuspensionSuspension Pattern #3 Form A 4-Sample H ester Experiment 50.3 HeptaneLinear alkane 98 3 Suspension Suspension Suspension Form A Form A4-Sample I Experiment 50.2 Isopropyl acetate Branched aliphatic 87 3Suspension Suspension Suspension Form A Form A 4-Sample J esterExperiment 49.6 Methyl Acetate Aliphatic ester 57 3 SuspensionSuspension Suspension Form A Form A 4-Sample K Experiment 50.3Methylethyl Asymmetric dialkyl 80 3 Suspension Suspension SuspensionForm A Form A 4-Sample L ketone ketone Experiment 5.2 2-Methyl THFAsymmetric cyclic 80 # Suspension Suspension Suspension Form A Form A4-Sample ether M Experiment 49.9 Nitromethane Dipolar aprotic 100 2Suspension Suspension Suspension Form A Form A 4-Sample N nitroExperiment 50.0 2-Propanol Branched aliphatic 83 3 Suspension SuspensionSuspension Insuff. mat. Insuff. 4-Sample O alcohol mat. Experiment 50.0Tetrahydrofuran Symmetric cyclic 66 2 Suspension Suspension SuspensionForm A Form A 4-Sample P ether Experiment 50.3 Toluene Alkyl aromatic111 2 Suspension Suspension Suspension Form A Form A 4-Sample Qhydrocarbon Experiment 49.7 Water Dihydrogen oxide 100 # SuspensionSuspension Suspension Pattern #4 Form A 4-Sample R

XRPD analysis of several moist pellets obtained from the suspensionequilibration experiment were inconsistent with Form A (refer to Table265 and FIG. 680 ). Analyses of the dried pellets were consistent withthe stable form (Form A).

Heat-Up/Cool-Down Crystallisations (HUCD) (Experiment 5)

For experimental procedure refer to Section F.2. The new metastableforms delivered are reported in Section D.5 (Experiment 5-Sample R1,Pattern #4) and Section D.7 (Experiment 5-Sample G1, Pattern #6).

Crystallisation from different solvents can be a useful method toinvestigate alternative polymorphic forms. Tabernanthalog sorbate salt(Experiment 1-Sample A2, Form A) was crystallised from the binarysolvents tabulated in Table 266.

A number of metastable forms were identified, Pattern #1 (Experiment5-Sample Q1), Pattern #4 (Experiment 5-Sample R1) and Pattern #6(Experiment 5-Sample G1), all of which readily reverted to Form A,during oven drying.

TABLE 266 Heat-up/cool-down crystallisations results. Co- KeyObservations XRPD XRPD Input Solvent solvents chemical (t = 1 (centri-(oven dried Input weights A (volumes functional b.p. ICH @ T = fuged, (@40° C., References referen (mg) (3.0 vol) Solvent B added, μl) groups (°C.) Classes 20° C.) wet) 20 h) Experiment 5- Taber- 74.7 Heptane Acetone1075 Symmetrical 56 3 Partial Form A Form A Sample A nanthalog ketoneExperiment 5- sorbate 75.2 tBME MeCN 875 Simple 82 2 Solid Form A Form ASample B salt dipolar- aprotic nitrile Experiment 5- 75.8 HeptaneChloro- 1150 Aromatic 131 2 Solid Form A Form A Sample C benzene halideExperiment 5- 75.3 Heptane DCM 1275 Chlorinated 40 2 Liquid Form A FormA Sample D hydrocarbon Experiment 5- 75.5 Heptane EtOH 300 Linear 78 3Partial Form A Form A Sample E aliphatic alcohol Experiment 5- 74.4Heptane EtOAc 1150 Aliphatic 75 3 Partial Form A Form A Sample F esterExperiment 5- 74.8 Heptane Ethyl 1325 Aldehyde 54 3 Partial Pattern #6Form A Sample G formate aliphatic ester Experiment 5- 74.4 HeptaneIsopropyl 2150 Branched 87 3 Partial Form A Form A Sample H acetatealiphatic ester Experiment 5- 74.7 tBME MeOH 150 Simple 65 2 Liquid FormA Form A Sample I aliphatic alcohol Experiment 5- 74.8 Heptane Methyl1475 Aliphatic 57 3 Partial Form A Form A Sample J acetate esterExperiment 5- 75.4 Heptane MEK 775 Asymmetric 80 3 Partial Form A Form ASample K dialkyl ketone Experiment 5- 75.4 Heptane MeTHF 1250 Asymmetric80 # Partial Form A Form A Sample L cyclic ether Experiment 5- 75.3Heptane Nitro- 1000 Dipolar 100 2 Liquid Form A Form A Sample M methaneaprotic nitro Experiment 5- 75.5 Heptane 2-Propanol 575 Branched 83 3Partial Form A Form A Sample N aliphatic alcohol Experiment 5- 75.4Heptane THF 650 Symmetric 66 2 Liquid Form A Form A Sample O cyclicether Experiment 5- 74.5 Heptane Toluene 3200 Alkyl 111 2 Partial Form AForm A Sample P aromatic hydrocarbon Experiment 5- 75.5 Water — Water100 # Solid Pattern #1 Form A Sample Q Experiment 5- 74.3 Acetone Water25 Water 100 # Liquid Pattern #4 Form A Sample R

Liquid Assisted (LAG) and Neat Pulverization (Experiment 7)

(For experimental procedure refer to Section F.2 and for experimentalcharacterization data that accompany this section refer to Sections H.1and H.2).

The products from water (Experiment 7-Sample B) and neat (Experiment7-Sample A) grinding were retrieved (a gum was obtained from TFE) andanalysed by XRPD. The phase obtained from neat grinding was consistentwith the input (Experiment 1-Sample A2, Form A, refer to FIG. 681 ), asno polymorphic changes was observed under these conditions. The phasedelivered from the pulverization in the presence of water (Experiment7-Sample B) matched Pattern #2 (refer to FIG. 684 ). DSC analyses ofboth products agreed with the XRPD data.

Considering that the oscillations input a large amount of kinetic andmechanical energy, designed to promote chemical and physical change, theproducts were additionally analysed by ¹H NMR spectroscopy (refer toFIG. FIG. 682 and FIG. 685 ). No significant chemical changes wereobserved.

The DSC profile of Experiment 7-Sample A neat is provided in FIG. 683and the DSC profile of Experiment 7-Sample B water is provided in FIG.686 .

Binary Solvent Evaporation Crystallisation (Experiment 6)

(For experimental procedure refer to Section F.2 and for experimentalcharacterization data that accompany this section refer to Section I.1).

Separate portions of Tabernanthalog sorbate salt (Experiment 1-SampleA2, Form A) were dissolved in a binary solvent mixture composed ofmethanol and water (Experiment 6-Sample A1), acetone (Experiment6-Sample B1), acetonitrile (Experiment 6-Sample C1), THE (Experiment6-Sample D1) and DCM (Experiment 6-Sample E1). Each vial was capped withaluminium foil, pierced, and allowed to stand undisturbed until theevaporation was completed.

The products were analysed by XRPD, and several differences wereobserved; some of which may be attributed to over emphasis of thereflection along a certain aspect, others may arise from differentcrystal structures. The product from methanol/water (Experiment 6-SampleA) was consistent with Pattern #1. ¹H NMR spectroscopy was chemicallyindistinguishable from Tabernanthalog sorbate salt (Experiment 1-SampleA2, Form A) in the initial analysis (t=0). A different powderdiffraction pattern is normally associated with crystal bonding;therefore Pattern #1 is assumed to be a hydrate.

Thermally promoted water-release caused facile re-organisation into thestable Form A while the transition enthalpy was not readily detected. Astrong crystal bonded hydrate obliterates the crystal when de-hydrated,which is obvious by DSC, while dehydration of a solely channel or pockethydrate affords an isomorphic de-hydrate, with little structuralreorganization (refer to Appendix #4, Section 1.4). Methanol was notdetected by ¹H NMR spectroscopy.

The binary solvent evaporation panel results are provided in Table 267and the picture of Experiment 6-Sample A, B, C, D and E after 7 days isprovided in FIG. 687 .

TABLE 267 Binary solvent evaporation panel results. Input Solvent XRPDInput weights A Solvent B b.p. ICH Yield (dried under Referencesreference (mg) (10 vol) (5 vol) (° C.) Classes (%) nitrogen) ExperimentTaber- 49.7 MeOH Water 100 3 101.0 Pattern #1 6-Sample A nanthalog ·Experiment Sorbate 50.0 MeOH Acetone 56 2 98.4 Pattern #1 > 6-Sample B(EXPERIMENT Form A > unk Experiment 1-SAMPLE 50.4 MeOH Acetonitrile 81 296.0 Form A 6-Sample C A2) Experiment 50.1 MeOH THE 65 2 94.6 Form A6-Sample D Experiment 50.3 MeOH DCM 40 3 95.6 Form A 6-Sample E

Powder pattern changed from Pattern #1 (Form B, refer to t=0, refer toFIG. 688 ) on standing (refer to t=8 days, refer to FIG. 691 ), into aform that resembled Form A, yet exhibited a small, sharp DSC endo.(Refer to 692), and coincident, small weight loss transition by TGA(FIG. 693 ), which is likely to be attributed to the incompleteequilibration of Pattern #1 into Form A. The DSC profile of Experiment6-Sample A1 T=0. De-hydration behaviour more consistent with channel orpocket hydration; no transition was evident into Form A is provided inFIG. 689 .

Overlaid of ¹H NMR spectra of Tabernanthalog Sorbate at t=0: Experiment6-Sample A1 (via evaporation from water and consistent with pattern #1,Form B, blue) and Experiment 1-Sample A2 (Form A, red). DMSO-d₆ used asdeuterated solvent is provided in FIG. 690 .

A DSC sample of Experiment 6-Sample A1 (t=8 days, refer to the reddiffraction pattern in FIG. FIG. 694 ) was heated to 80° C., cooledunder nitrogen to 20° C. and the residue was analysed by XRPD (blackpowder pattern in FIG. FIG. 694 ) was congruent with Form A.

Experiment 6-Sample A1 (t=8 days) specimen is Form A>Pattern #1 (FormB), because the phase transition was under equilibration, and if leftstanding for an extended time, the mixed component would have whollyreverted to Form A.

DSC profile of Experiment 6-Sample A1 Rep. is provided in FIG. 695 .

The best course of action was to definitively characterise the proposedhydrate (Pattern #1, Form B) via SCXRD, as this will enable us toconfidently assign the mode of hydration The crystals from the binarysolvent evaporation crystallisation experiment Experiment 6-Sample A1were not suitable. Examination of previous crystals of Pattern #1 (FormB, Experiment 5-Sample Q2), obtained via heat-up/cool-down from water(refer to Section C.2) were judged to be small to sufficiently diffract;therefore, an attempt to re-grow and maintain the crystals water‘wetted’, prior to the structure determination in Section C.2.

The PLM of Experiment 6-Sample A1 (normal polarisation, ×2 magn.) isprovided in FIG. 696 .

Reproducibility of HUCD Crystallisations

For experimental procedure refer to Section F.2.

Patterns #1 and 6 (Experiment 8)

(For experimental characterisation data that accompany this sectionrefer to Sections H.3) Initial heat-up/cool-down crystallisations(Experiment 5) delivered Patterns #1 (Form B, water) and Pattern #6(heptane/ethyl formate). The selected experiments were repeated toprovide enough of these forms for full characterisation.

Oven-drying of the output was avoided as it previously promotedformation of Form A, therefore, isolation was performed via filtrationthrough a Hirsch funnel. XRPD diffractograms of moist pellets(Experiment 8-Sample A1 and Experiment 8-Sample B1) were obtained 30 minafter filtration. Samples were left to dry for ca. 2 h under N2 flux atambient temperature; however, Pattern #1 (Form B) was altered afterdrying (Experiment 8-Sample A2) and Pattern #6 Experiment 8-Sample),crystallised as Form A.

Experiment 8-Sample A2 (after drying under gentle nitrogen flux) wasdifferent from the target Pattern #1 (Form B) and Form A. Exhibited anonly small weight loss of −0.5% w/w by TGA.

Designated Pattern #7 (Form D). ¹H NMR spectroscopy of Experiment8-Sample A2 (Pattern #7) was a different chemical composition,attributed to reaction with ethyl formate. This occurred during theoven-drying process. Evaluated it for potential SC-XRD by PLM and werenot suitable.

The results are summarized in Table 268. The overlaid of ¹H NMR spectraof Tabernanthalog Sorbate samples: Experiment 1-Sample A2 (Form A),Experiment 8-Sample A1 (wet pellet, Pattern #1, Form B), Experiment8-Sample A2 (dried under N2 purge, different from Pattern #1, Form B andForm A) and Experiment 5-Sample Q1 (Pattern #1, Form B crystallised fromwater) is provided in FIG. 697 . The overlaid of ¹H NMR spectra ofTabernanthalog Sorbate samples: Experiment 1-Sample A2 (Form A),Experiment 8-Sample B1 (wet pellet, Form A), Experiment 8-Sample B2(dried under N2 purge, Form A) and Experiment 5-Sample G1 (Pattern ′#6,crystallised from EtOAc/heptane) is provided in FIG. 698 .

TABLE 268 Summary of results. Co- XRPD XRPD Input Solvent solvents(centri- (under Input weights A (3.0 Solvent (volumes Yield Targetfuged, nitrogen References reference (mg) vol) B added, μl) % form wet)flow) Experiment EXPERIMENT 74.7 Water — 225 53.3 Pattern #1 Pattern #1Chemical 8-Sample A 1-SAMPLE composition A2 altered Experiment 75.2Heptane Ethyl 1325 43.6 Pattern #6 Form A Form A 8-Sample B formate

Patterns #2, #3, #4 and #5 (Experiment 9)

(For Companion Analytical Data Refer to Section D.1).

Suspension equilibration at 40° C. for 7 days was repeated, as thesewere the conditions used previously, aiming to generate #2 (water), #3(ethyl formate), Pattern #4 (from water) and Pattern #5 (DCM) for TGanalyses.

Preparation of Pattern #2 was successful; however, preparations ofPattern #3, Pattern #4 and Pattern #5 were not successful, givinginstead Form A, Pattern #2 and a very disordered product, respectively.The summary of the results are provided in Table 269.

TABLE 269 Summary of results. Sol- Obser- Obser- ¹H vent Obser- vationsvations XRPD XRPD NMR Input Input (1 part, vations (t = (t = (IPC, (post(solvent Refer- refer- weight 5 vol (t = 0 @ 1 d @ 5 d @ 5 d, Filter DSCTGA content, ences ence (mg) total) 20° C.) 20° C.) 20° C.) Target wet)dried) (Jg{circumflex over ( )} − 1) (% w/w) % w/w) Experi- Form 75.1Water Sus- Sus- White Pattern Pattern Pattern Onset: Onset: ND ment 9- Apension pension Sus- #2 #2 #2 78.10° C. 70.18° C. Sample A pension(−118.50 ) (−2.5400) Onset: Onset: 144.81° C. 88.73° C. (−113.28)−1.4218% Sol- Obser- Obser- ¹H vent Obser- vations vations XRPD XRPD NMRInput Input (1 part, vations (t = (t = (IPC, (post (solvent Refer-refer- weight 5 vol (t = 0 @ 1 d @ 5 d @ 5 d, Filter DSC TGA content,ences ence (mg) total) 40° C.) 40° C.) 40° C.) Target wet) dried)(Jg{circumflex over ( )} − 1) (% w/w) % w/w) Experi- Form 75.2 EtOAcSus- Sus- White Pattern Form A Form A — — — ment 9- pension pension Sus-#3 Sample C pension Experi- A 74.8 Water Sus- Sus- Brown Pattern PatternPattern Onset: Onset: ND ment 9- pension pension Sus- #4 #2 #2 54.68° C.72.90° C. Sample B pension (−4.68) (−2.9321) Onset: Onset: 145.44° C.175.16° C. (−94.02) (−23.4734%) Experi- 75.0 DCM Sus- Sus- Beige PatternPattern v. Dis- insuf- insuf- insuf- ment 9- pension pension Sus- #5 #5ordered ficient ficient ficient Sample D pension Pattern materialmaterial material #5 (d- (gummy) (gummy) (gummy) spacings to higherangle)

Stability at 95% RH (KNO₃) at 20° C. (Experiment 10)

(For experimental data that accompany this section refer to refer toSection F.2 and for characterization data refer to Section 1.2).

Tabernanthalog sorbate salt Experiment 10-Sample A (open vial) andExperiment 10-Sample B (open vial, double-bagged in polyethene bags tiedtightly with cable ties) were placed in the humidity chamber (FIG. 698A)

The samples were maintained under equilibrium humidity of 95% RH at 20°C. and monitored at 5 day by XRPD and 10 day time points by ¹H NMR,XRPD, DSC, TGA and PLM.

Form A converted to Pattern #2 after 5 days in the open vial (Experiment10-Sample A1) and after 10 days in the closed vial (Experiment 10-SampleB2), for companion analytical data refer to Appendix #2 (refer toSection 1.2; absorbent was stable at 40° C./75% RH, 10 days (refer toExperiment 6 of Example 8). DVS is reproduced in Appendix #5 (refer toSection 1.5).

DVS analyses of Form A (Performed on batch reference: Experiment11-Sample -A1) To determine whether Form A underwent form change at high% RH, DVS residues of Form A, from 0 to 80% RH and 0 to 90% RH, wereexamined. The specimens were equilibrated to constant mass, at 80% and90% RH set-points, removed, placed in a capped vial, and analysed byXRPD and DSC. Based on the SC-XRD at 100 K, no regular voids in thecrystal structure were large enough to accommodate non-crystal-bonded,molecular water with minimum probe radius of 1.4 Å. DVS data ofExperiment 1-Sample A2 is provided in FIG. 699 .

DVS Analyses of Form A to 80% RH

The analytical data of the specimen that was retrieved from theexperiment performed from 0 to 80% RH are reported in FIG. 700 (XRPD)and in FIG. 701 (DSC). The powder diffraction pattern post-DVS (blackdiffractogram) was consistent with Form A (red diffractogram). The m.p.of specimen at 80% RH was also consistent with Form A.

DVS Analyses of Form A to 90% RH

The powder diffraction pattern of the specimen retrieved at 90% RHmatched the reference batch of Form A (refer to FIG. 702 ). Th DSCthermogram of the specimen was consistent with Form A (refer to FIG. 703).

Examination of Variability of Fusion Temperature

The factors that were assessed to explain the observed variability infusion temperature found amongst Form A samples were sample loading,preferred orientation and particle size/homogeneity (Table 271). A weakrelationship between sample loading and melt onset was observed, theremainder of the factors examined, appeared to be unrelated.

Samples from the evaporation panel exhibited over emphasis ofreflections at 7.5°, 28.5° and 29.5° 2-theta (refer to FIG. 704 ,Experiment 6-Sample C1, -D1, E1). This property did not appear to berelated to the variance in fusion temperature observed by DSC.

TABLE 271 Fusion temperature of various batches of Form A (25-220° C. at10° C. min⁻¹).* Sample Melt melt size onset Peak Endset enthalpyExperiment (mg) (° C.) (° C.) (° C.) (Jg⁻¹) A1270-20-V2 4.2 143.9 148.8152.0 −84.1 Experiment 13-Sample 2.5 139.9 142.5 144.5 −105.8 C1Experiment 1-Sample 3.4 140.0 142.5 144.1 −106.7 A2 Experiment 6-Sample5.5 144.7 148.8 151.0 −100.5 C1 Experiment 6-Sample 3.5 144.0 148.0150.2 −105.7 D1 Experiment 6-Sample 4.3 145.0 148.8 151.6 −105.7 E1Experiment 7-Sample A 2.4 144.4 146.8 148.5 −122.5 neat Experiment7-Sample B 3.5 144.5 146.8 148.4 −115.1 water Experiment 8-Sample 3.5141.8 144.3 146.0 −98.0 B2 Experiment 11-Sample 5.7 145.8 149.8 152.5−92.3 A1 Minimum 139.9 142.5 144.1 −122.5 Maximum 145.8 149.8 152.5−84.1 Mean 143.4 146.7 148.9 −103.4 Standard Deviation 2.1 2.7 3.1 11.5Sample Variance 4.4 7.3 9.7 132.1 *The DSC data reported in Table 271derived from samples that DSC analyses were collected for Form A. Table272 includes all the samples that resembled Form A, for which DSC datawere not collected for some of them.

SC-XRD

Form A

For experimental data that accompany this section refer to Section F.2and for characterization data refer to Section 1.7.

Crystal Data for Experiment 11-Sample A1 (refer to FIG. 705 ).C20H2₆N2O₃, M_(r)=342.43, monoclinic, P2₁/c (No. 14), a=9.3410(3) Å,b=6.4173(2) Å, c=30.5108(12) Å, b=95.374(3)°, a=g=900, V=1820.90(11) Å³,T=100(2) K, Z=4, Z′=1, m(Cu K_(a))=0.675 mm⁻¹, 13832 reflectionsmeasured, 3694 unique (R_(int)=0.0462) which were used in allcalculations. The final wR₂ was 0.2098 (all data) and R_(I) was 0.0826(I≥2 s(I)).

Th asymmetric structure contains one API molecule one sorbate ion.Hydrogen bonding takes place between both oxygen molecules on thesorbate ion (refer to FIG. 720 ). One to N1 (tryptamine nitrogen atom)of one API molecules, the other to N2 (hydro-azepine nitrogen atom) of aseparate API molecule.

The hydrogen bonding network of Tabernanthalog sorbate salt (Experiment11-Sample A1, Form A) is shown in FIG. 706 and FIG. 707 .

Due to hydrogen bonding present in the structure builds up chainsbetween API and salt molecule, which causes stacking of API and sorbatemolecules closely packed to one another (refer to FIG. 707 ). This leadsto less free space in the crystal structure and void radius of only ˜0.9Å, much smaller than the 1.4 required for a water molecule to occupy.Hydrogen bond lengths between Sorbates and API are N1 (indole) O3, 2.857Å (hydrogen bond), N2 (hydroazepine)-O2, 2.7015 Å (salification hydrogenbond). Sorbate molecule is disordered, and bond lengths stated are anaverage of the two mapped positions (refer to FIG. 708 ).

The calculated powder diffraction pattern is depicted in FIG. 709 . Thecomparison of the simulated and experimental powder diffraction patternis depicted in FIG. 710 .

Hydrate

Crystal Data of Experiment 12-Sample A2 (refer to FIG. 711 ).C₂₀H28N₂O₄, M_(r)=360.44, monoclinic, P2_(1/c) (No. 14), a=16.07470(10)Å, b=12.14150(10) Å, c=10.85080(10) Å, b=109.2390(10)°, a=g=900,V=1999.49(3) Å³, T=100(2) K, Z=4, Z′=1, m(Cu K_(a))=0.676 mm⁻¹, 51305reflections measured, 3786 unique (R_(int)=0.0483) which were used inall calculations. The final wR₂ was 0.0874 (all data) and R_(I) was0.0347 (I≥2 s(I)).

Unit cell contains 1 API, 1 sorbate, 1 water molecule (refer to FIG. 712) with same space group setting P2₁C as Form A. Hydrogen bonding takesplace between water molecule, API and sorbates (refer to FIG. 713 ).Salification of the API occurs at N2 (refer to FIG. 714 ).

Void space analysis, maximum void radius=0.98 Å, much smaller than 1.4 Årequired for another water molecule to be present (refer to FIG. 715 ).Change in packing compared to Form A due to the hydrogen bonding fromthe water molecule (refer to FIG. 716 ). Powder pattern of Experiment12-Sample A2 contained a mixture of patterns, and overlap is observedbetween simulated powder pattern (refer to FIG. 717 and FIG. 718 ).

D. Summary of Forms

1. Tabernanthalog Sorbate Salt Form A (Experiment 1-Sample A2)

TABLE 272 List of experiments that resulted in Form A. Form A Experiment1- Experiment 2-Sample Experiment 4-Sample F2 Sample A2 J1 Experiment 6-Experiment 2-Sample Experiment 4-Sample L2 Sample D1 H1 Experiment 6-Experiment 2-Sample Experiment 4-Sample Q1 Sample A1 M2 Experiment 6-Experiment 2-Sample Experiment 5-Sample A1 Sample E1 Q1 Experiment 3-Experiment 3-Sample Experiment 5-Sample B1 Sample I1 L1 Experiment 4-Experiment 3-Sample Experiment 5-Sample B2 Sample N1 P1 Experiment 6-Experiment 3-Sample Experiment 5-Sample E2 Sample C1 N1 Experiment 6-Experiment 3-Sample Experiment 5-Sample F2 Sample B1 Q1 Experiment 2-Experiment 4-Sample Experiment 5-Sample H2 Sample A2 G1 Experiment 2-Experiment 4-Sample Experiment 5-Sample J2 Sample A2 F1 Experiment 2-Experiment 4-Sample Experiment 5-Sample K2 Sample B2 M1 Experiment 2-Experiment 4-Sample Experiment 5-Sample P1 Sample C1 L1 Experiment 2-Experiment 4-Sample Experiment 5-Sample J1 Sample C2 P1 Experiment 2-Experiment 4-Sample Experiment 5-Sample C1 Sample D2 J1 Experiment 2-Experiment 4-Sample Experiment 5-Sample A2 Sample G2 A1 Experiment 2-Experiment 4-Sample Experiment 5-Sample C2 Sample J2 B1 Experiment 2-Experiment 4-Sample Experiment 5-Sample I2 Sample N1 K1 Experiment 2-Experiment 4-Sample Experiment 5-Sample L2 Sample N2 M2 Experiment 2-Experiment 4-Sample Experiment 5-Sample P2 Sample Q2 N2 Experiment 2-Experiment 4-Sample Experiment 5-Sample D2 Sample R1 P2 Experiment 2-Experiment 4-Sample Experiment 8-Sample B2 Sample R2 Q2 Experiment 2-Experiment 4-Sample Experiment 9-Sample C1 Sample S2 A2. Experiment 2-Experiment 4-Sample Experiment 10-Sample B1 Sample E1 B2. (5days)Experiment 2- Experiment 4-Sample Experiment 11-Sample A1 Sample E2 J2Experiment 2- Experiment 4-Sample Experiment 13-Sample C1 Sample D1 K2Experiment 2- Experiment 4-Sample Sample P1 G2 Experiment 2- Experiment4-Sample Sample P2 O2

The ¹H NMR spectrum of Experiment 1-Sample A2 in DMSO-d₆ used asdeuterated solvent is provided in FIG. 719 . The Q NMR assay ofExperiment 1-Sample A2 in DMSO-d₆ used as deuterated solvent. 99.900 w/wassay is provided in FIG. 720 . The overlay of ¹H NMR spectra ofExperiment 1-Sample A2 (red) and Experiment 13-Sample C1 (referencepattern, black) is provided in FIG. 409 .

The DSC profile of Experiment 1-Sample A2 is provided in FIG. 563 . Theoverlay of DSC profiles of Experiment 1-Sample A2 (black) and Experiment13-Sample C1 (reference pattern, red) is provided in FIG. 410 .

The TGA profile of Experiment 1-Sample A2 is provided in 564. Theoverlaid of TGA profiles of Experiment 1-Sample A2 (black) andExperiment 13-Sample C1 (reference pattern, red) is provided in FIG. 411.

The HPLC, profile of Experiment 1-Sample A2 is provided in FIG. 566 .The polarised light microscopy (PLM) of Experiment 1-Sample A2 isprovided in FIGS. 567-570 .

The XRPD profile of Experiment 1-Sample A2 is provided in FIG. 564 .

TABLE 273 Peak angle data of Experiment 1-Sample A2. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%)  5.7 15.53 100 11.4  7.75 4022.8  3.89 11

The overlaid of XRPD profiles of Experiment 1-Sample A2 (black) andExperiment 13-Sample C1 (reference pattern, red) is provided in FIG. 412.

The DVS Experiment 1-Sample A2, kinetic plot and isotherm analysisreport is provided in FIG. 455 . The DVS Experiment 1-Sample A2,isothermal plot is provided in FIG. 455 .

The XRPD profile of Experiment 1-Sample A2_post DVS is provided in FIG.458 and Table 274.

TABLE 274 Peak angle data of Experiment 1-Sample A2-post DVS. Reportedonly peaks >10%. Rel. Intensity values calculated based on Net.Intensity values. 2-θ (º) d Value Rel. Intensity (%) 5.7 15.37 100 10.68.36 15 11.5 7.70 41 18.9 4.68 22 22.8 3.90 17 24.5 3.63 12 24.7 3.60 23

2. Tabernanthalog Sorbate Salt Form B (Pattern #1, Experiment 2-SampleS1, A270-060-Q1, Experiment 6-Sample A1, Experiment 8-Sample A1Experiment 12-Sample A2)

A list of experiments that resulted in Form B (Pattern #1) is providedin Table 275. The characterization is provided in FIGS. 721-728A andTables 276 and 277.

TABLE 275 List of experiments that resulted in Form B (Pattern #1). FormB (PATTERN #1) Experiment 2-Sample S1 Experiment 6-Sample A1 Experiment8-Sample A1 Experiment 5-Sample Q1 Experiment 12-Sample A2 

TABLE 276 Peak angle data of Experiment 2-Sample S1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 7.5 11.73 100 15.1 5.85 15

TABLE 277 Peak angle data of Experiment 6-Sample A1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 7.6 11.7 100 15.1 5.85 13

3. Tabernanthalog Sorbate Salt Form C (Pattern #2, Experiment 3-Sample Rand Experiment 10-Sample A2)

The list of experiments that resulted in Form C (Pattern #2) is providedin Table 278. The characterization is provided in FIGS. 729-736 andTables 279 and 280.

TABLE 278 List of experiments that resulted in Form C (Pattern #2). FormC (Pattern #2) Experiment 3-Sample R1 Experiment 9-Sample A1 Experiment10-Sample A1 (5 days) Experiment 10-Sample A2  Experiment 10-Sample B2 Experiment 9-Sample A2 Experiment 9-Sample B2 Experiment 7-Sample B(water) Experiment 9-Sample B1

TABLE 279 Peak angle data of Experiment 3-Sample R1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 5.7 15.37 100 11.5 7.67 24

TABLE 280 Peak angle data of Experiment 10-Sample A2. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 5.7 15.41 100 11.2 7.90 1411.5 7.68 28 13.9 6.35 11 16.7 5.30 28 17.3 5.11 28 17.8 4.99 19 18.54.80 21 18.7 4.74 21 20.1 4.41 12 22.4 3.96 95 29.7 3.01 10

4. Tabernanthalog Sorbate Salt Pattern #3 (Experiment 4-Sample H1)

The list of experiments that resulted in Pattern #3 (mixture of Form A,Pattern #1 and Pattern #6) is provided in Table 281. Thecharacterization is provided in FIG. 737 and Table 282.

TABLE 281 List of experiments that resulted in Pattern #3 (mixture ofForm A, Pattern #1 and Pattern #6). Pattern #3 Experiment 4-Sample H1

TABLE 282 Peak angle data of Experiment 4-Sample H1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 5.7 15.36 100 5.7 15.59 797.3 12.18 98 7.4 11.87 36 9.5 9.35 13 10.6 8.33 19 11.5 7.70 60 11.57.71 73 14.5 6.10 15 18.9 4.68 53 22.8 3.89 13 23.0 3.86 24 24.7 3.60 2524.8 3.59 28 27.0 3.30 10 29.3 3.04 10 29.7 3.00 15

5. Tabernanthalog Sorbate Salt Pattern #4 (Experiment 5-Sample R1)

The list of experiments that resulted in Pattern #4 is provided in Table283. The characterization is provided in FIG. 738 and Table 284.

TABLE 283 List of experiments that resulted in Pattern #4. Pattern #4Experiment 5-Sample R1

TABLE 284 Peak angle data of Experiment 5-Sample R1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 5.9 14.90 100 5.8 15.10 5111.3 7.83 14 11.6 7.60 17 16.8 5.27 23 17.5 5.08 17 17.9 4.96 16 18.64.78 20 18.8 4.72 17 20.2 4.38 10 22.5 3.94 66

6. Tabernanthalog Sorbate Salt Pattern #5 (Experiment 4-Sample E1)

The list of experiments that resulted in Pattern #5 is provided in Table285. The characterization is provided in FIG. 739 and Table 286.

TABLE 285 List of experiments that resulted in Pattern #5. Pattern #5Experiment 4-Sample E1

TABLE 286 Peak angle data of Experiment 4-Sample E1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 7.7 11.53 34 8.4 10.46 1210.9 8.10 11 12.5 7.05 13 14.1 6.28 100 14.7 6.01 13 15.4 5.75 30 15.75.65 12 16.5 5.37 78 17.9 4.96 13 18.3 4.85 39 18.6 4.77 13 19.2 4.61 3319.9 4.46 14 20.5 4.34 62 20.8 4.26 51 21.2 4.19 42 21.8 4.07 12 22.93.88 21 23.2 3.82 37 24.3 3.66 25 25.4 3.50 16 26.2 3.39 15 27.4 3.25 4028.5 3.13 14 28.7 3.10 18 29.8 3.00 13 31.1 2.88 18 31.7 2.82 11 32.52.75 11 32.6 2.75 13

7. Tabernanthalog Sorbate Salt Pattern #6 (Experiment 5-Sample G1)

The list of experiments that resulted in Pattern #6 is provided in Table287. The characterization is provided in FIG. 740 and Table 288.

TABLE 287 List of experiments that resulted in Pattern #6. Pattern #6Experiment 5-Sample G1

TABLE 288 Peak angle data of Experiment 5-Sample G1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 5.7 15.46 10 7.2 12.19 100

E. Conclusions

SCXRD data for Tabernanthalog sorbate salt (Experiment 11-Sample A1,Form A, anhydrous) were obtained, as well as for Tabernanthalog sorbatesalt·H₂O (Experiment 12-Sample A2, mainly Pattern #1, assigned Form B,metastable hydrate, unique XRPD, evolves into Form C, enriched specimenwith the crystallographer.

The metastable forms identified during the polymorph screen were:

-   -   Experiment 10-Sample A2 (Pattern #2, assigned Form C, unary        hydrate); assumed to be crystal bonded, unique XRPD, not        isomorphic with Form A, specimen.    -   Experiment 4-Sample E1 (Pattern #3) converted into Form A.    -   Experiment 4-Sample R1 (Pattern #4) converted into Form A and        was not suitable for SC-XRD.    -   Experiment 4-Sample E1 (Pattern #5) converted into Form A.    -   Experiment 5-Sample G1 (Pattern #6) converted into Form A.

The metastable forms were obtained via suspension equilibration or HUCDand the wet pellet, readily underwent conversion into Form A duringdrying.

Tabernanthalog sorbate salt (Form A) was subjected to 20° C./95% RH,where it was converted to Pattern #2 after 5 days in the open vial(Experiment 10-Sample A1) and after 10 days in the closed vial(Experiment 10-Sample B2).

F. Experimental 1. Instrumentation DSC

A Mettler Toledo DSC 3 instrument was used for the thermal analysisoperating with STARe™ software. The analysis was conducted in openaluminium pans (40 μl), under nitrogen and sample sizes ranged from 1 to10 mg. Typical analysis method was 20 to 250° C. at 10° C./minute.

Alternatively, a Mettler Toledo DSC1 with auto-sampler instrument wasused for the thermal analysis operating with STARe™ software. Theanalysis was conducted in open aluminium pans (40 μl), under nitrogenand sample sizes ranged from 1 to 10 mg. Typical analysis method was 25to 300° C. at 10° C./minute.

DVS

The moisture sorption properties of the feed API were analysed by DVSIntrinsic instrument (Surface Measurement System). Approximately 20 to50 mg of API was weighed onto an aluminium pan and loaded into theinstrument equilibrated at 25° C. The sample was equilibrated under adry atmosphere (0% relative humidity) for 60 minutes, before increasingthe humidity from 0% to 30% at 5% step increment and from 30% to 90% at10% step increment. A desorption cycle was also applied from 90% to 30%(10% step decrement) and from 30% to 0% (5% step decrement). A rate ofchange in mass per time unit (dm/dt) of 0.002%/min was set as theequilibrium parameter. Kinetic and isotherm graphs were calculated.

LC-MS

Routine Liquid Chromatography-Mass Spectrometry (LC-MS) data werecollected using the Agilent 1260 Infinity II interfaced with 1260Infinity II DAD HS and Agilent series 1260 Infinity II binary pump.

The instrument used a single quadrupole InfinityLab MSD. The instrumentwas calibrated up to 2000 Da.

LC-MS method parameters:

Inj.vol: 5 μl Detection: UV @ 254 nm Mobile Phase A: Acetonitrile+0.1%TFA/H₂O 95:5 Mobile Phase B: Acetonitrile+0.05% TFA/H₂O 5:95

Time (min) % A % B 0.0 100 0 1 100 0 10.00 0 100 10.01 100 0 12.00 100 0Flow Rate: 1 ml/minColumn temperature: 30° C.Run time 12 minutes.

FT-IR

FT-IR Spectra were acquired using a PerkinElmer Frontier FT-IRspectrometer. Samples were analysed directly using a universal ATRattachment in the mid and far frequency ranges; 4000 to 30 cm⁻¹. Spectrawere processed using Spectrum software. Standard KBr windows are usedfor mid-IR applications; polyethylene and polyethylene/diamond windowsare used for operation in the far-IR. Further capabilities of theinstrument include a liquid flow cell with ZnSe windows used for rapidmonitoring of reactions. This couples with time-based software whichallows time-resolved measurements to be taken.

¹H NMR

¹H NMR spectra were acquired using a Bruker 400 MHz spectrometer anddata was processed using Topspin. Samples were prepared in DMSO-d₆ attypical concentrations of 10 to 20 mg/ml and up to 50 mg/ml for ¹H NMRw/w assay and calibrated to the corresponding non-deuterated solventresidual at 2.50 ppm.

¹H NMR assay

Assays (w/w) of API by ¹H NMR spectroscopy were measured by the projectchemist using Topspin. Internal standard 2,3,5,6-terachloronitrobenzene(TCNB, ca. 20 mg, F.W. 260.89) were dissolved in DMSO-d₆ (2.0 ml) andthe ¹H NMR spectrum was acquired using an extended relaxation method.

HPLC(MET/CR/2616)

HPLC data was acquired using an Agilent HPLC instrument. Samples werediluted to 1 mg/mL concentration in H₂O/DMSO (1/1, v/v).

Method Parameters: Column: Halo C18, 150×4.6 mm, 2.7 μm

Inj. volume: 5 μL

Detection: UV @ 212 nm

Mobile Phase A: 0.1% TFA in water/acetonitrile 95/5 v/vMobile Phase B: 0.05% TFA in water/acetonitrile 5/95 v/v

Time (min) % A % B 0.0 100 0 2.0 100 0 25.0 50 50 30.0 0 100 32.0 0 10032.1 100 0 37.0 100 0Flow rate: 1 mL/minColumn temperature: 30° C.Run time: 37 minutesIntegration time: 32 minutesWash vial or syringe wash: Sample diluentCrystal 16 apparatus

A Technobis instrument that is used to program heat up and cooled downramps at specific rates, whilst measuring the transmissivity of thecontents of the vials. The response is reported in % and denotes theclear and cloud points at specific concentrations. The instrument offers4 chambers where 4 vials can be placed.

TGA

A Mettler Toledo TGA-2 instrument was used to measure the weight loss asa function of temperature from 25 to 500° C. The scan rate was typically5 or 10° C. per minute. Experiments and analysis were carried out usingthe STARe™ software. The analysis was conducted in 100 μl open aluminiumpans, under nitrogen and sample sizes ranged from 1 to 10 mg.

XRPD

X-ray powder diffraction (XRPD) analysis was carried out using a BrukerD2 Phaser powder diffractometer equipped with a LynxEye detector. Thespecimens underwent minimum preparation but, if necessary, were lightlymilled in a pestle and mortar before acquisition. The specimens werelocated at the centre of a silicon sample holder within a 5 mm pocket(ca. 5 to 10 mg). The samples were continuously spun during datacollection and scanned using a step size of 0.02°2-theta (2θ) betweenthe range of 4° to 40° 2-theta or 5° to 60° 2-theta. Data were acquiredusing either 3 minute or 10-minute acquisition methods. BrukerDiffrac.Suite was used to process the data.

2. General Procedures Preparation of Form A

Experimental reference: Experiment 1-Sample A2

Tabernanthalog (native) (3.87 g, 1.0 wt) and sorbic acid (2.07 g, 0.53wt, 1.1 equiv) were were dissolved in ethanol (11 ml, 3.0 vol) at 85 to90° C. The clear brown solution was left to cool down to ambient (solidwas observed) before standing undisturbed under sub-ambient conditionsfor ca 18 h. The product was isolated by filtration, de-liquored andleft to pull dry under steady nitrogen flux for ca. 3 h. No wash cyclewas applied. The product was off-loaded from the filtration assembly andwas oven-dried under vacuum at 40° C. for ca 18 h to afford Experiment1-Sample A2 (5.05 g, 87% uncorr. yield, 0.2% w/w ethanol).

Preparation of Form B (Form B (Pattern #1) was Initially Observed in theQualitatively Solubility Study (Experiment 2-Sample S1))

Experimental Reference: Experiment 5-Sample Q1 and Experiment 8-SampleA1 (HUCD)

Tabernanthalog sorbate salt (1.0 wt, Experiment 1-Sample A2, Form A) wasweighed out in a vial and water (3.0 vol) was charged and warmed totemperature. The clear solution was left to cool down and standundisturbed under sub-ambient conditions for several days. Aftercrystallisation was judged complete, the product was isolated bycentrifugation and the pellet was analysed by XRPD, which matched Form B(Pattern #1, Experiment 5-Sample Q1). The phase of the wet filter cakewas consistent with Form B (Pattern #1, Experiment 8-Sample A1)

Experimental Reference: Experiment 6-Sample A1 (Binary SolventEvaporation Crystallisation)

Tabernanthalog sorbate salt (ca. 50 mg, 1.0 wt, Experiment 1-Sample A2,Form A) was dissolved in a binary solvent mixture composed of methanol(500 μl) and water (250 μl). The vial was capped with aluminium foil,pierced, and allowed to stand undisturbed until the evaporation iscompleted.

Preparation of Form C

Experimental Reference: Experiment 3-Sample R1 and Experiment 9-SampleA1 and -A2 (Suspension Equilibration at 20° C.)

Tabernanthalog sorbate salt (1.0 wt, Experiment 1-Sample A2, Form A) wascharged to a vial and water (5 vol) was subsequently added. Thesuspension was stirred at 20° C. for 6 days, prior to isolating theproduct by centrifugation (Experiment 3-Sample R1). XRPD analysis of thewet pellet showed conversion from Form A to Pattern #2. The latter phasedid not revert to Form A upon drying on the filter (Experiment 9-SampleA2).

Experimental Reference: Experiment 9-Sample B1 and -B2 (SuspensionEquilibration at 40° C.)

Tabernanthalog sorbate salt (1.0 wt, Experiment 1-Sample A2, Form A) wascharged to a vial and water (5 vol) was subsequently added. Thesuspension was stirred at 40° C. for 5 days, prior to isolating theproduct by filtration. XRPD analysis of the wet and dried filter cakeconfirmed the conversion of Form A to Pattern #2.

Experimental reference: Experiment 10-Sample A1 (-A2) and Experiment10-Sample B2 (Stability at 95% RH (KNO₃) at 20° C.)

Tabernanthalog sorbate salt (ca. 100 mg, 1.0 wt, Experiment 1-Sample A2,Form A) was weighed out in an open-capped vial and was placed inside ahumidity chamber at 95% RH at 20° C. At t=5 d, Form A converted toPattern #2.

Tabernanthalog sorbate salt (ca. 100 mg, 1.0 wt, Experiment 1-Sample A2,Form A) was weighed out in an open-capped vial, which was subsequentlydouble-bagged in polyethene bags tied tightly with cable ties and wasplaced inside a humidity chamber at 95% RH at 20° C. At t=10 d, Form Aconverted to Pattern #2.

Experimental reference: Experiment 7-Sample B (LAG in water)

Tabernanthalog sorbate salt (50 mg, Experiment 1-Sample A2, Form A) waspulverised in the presence of water (25 μl, η=0.5), a single 7 mm steelbead was added to the reactor, after which they were sealed, andoscillated for 30 minutes at 8.0 Hz (ca. 500 rpm).

Qualitative Solubility Screen (Experiment 2)

Tabernanthalog sorbate salt (Experiment 1-Sample A2, Form A, 25 mg, 1wt) was weighed out in 22 separate vials to qualitatively examine thesolubility in an array of diverse solvents. The solubility was testedinitially at 5 vol at 20° C., 40° C. and reflux. If insoluble at 5 vol,the solvent quantity was increased to 10 vol, 15 vol and 20 vol of therespective solvent. The suspensions that occurred upon cooling down werecentrifuged and the solvent wet pellets were analysed by XRPD.

The insoluble suspensions were additionally worked up for XRPD analysis.The resultant powder patterns were subsequently cross-referenced againstthe input supplied material.

Suspension equilibration (Experiments 3 and 4)

Portions of Tabernanthalog sorbate salt (50 mg, 1.0 wt, Experiment1-Sample A2, Form A) were charged to separate vials. The relevantsolvent (5 vol) was added to the appropriate vial and the suspensionswere stirred and warmed to the predetermined temperature with stirring.Once equilibration was completed (10 days at 20° C.), stirring wassuspended and the products were isolated by centrifugation, wet anddried (at 40° C. under reduced pressure) pellets were analysed by XRPD.

Heat-up/cool down crystallisation screen (Experiment 5)

Portions of Tabernanthalog sorbate salt (ca 75 mg, 1.0 wt, Experiment1-Sample A2, Form A) were charged to separate vials. The relevantsolvent (0.225 ml, 3.0 vol) was added to the appropriate vial and thesuspensions were stirred and warmed to temperature. If dissolution wasnot observed, further solvent was added until the solute dissolved, oraliquots of a secondary co-solvent were added to complete dissolution.Once dissolved, the solutions were left to cool down and standundisturbed under sub-ambient conditions for several days. Aftercrystallisation was judged complete, the products were isolated bycentrifugation and the pellets were dried at 40° C. under reducedpressure. Products from the crystallisation (wet and dry) were initiallyanalysed by XRPD (9-minute method), further analyses of certain productswere performed by ¹H NMR, DSC and TGA, if the diffraction patternindicated differences.

Liquid Assisted (LAG) and Neat Pulverization (Experiment 7)

Separate portions of Tabernanthalog sorbate salt (50 mg, Experiment1-Sample A2, Form A) were pulverised in the presence of water (25 μl,η=0.5), trifluoroethanol (25 μl, η=0.5) as well as under neat grindconditions.

A single 7 mm steel bead was added to each reactor, after which theywere sealed, and oscillated for 30 minutes at 8.0 Hz (ca. 500 rpm).

Binary Solvent Evaporation Crystallisation (Experiment 6)

Separate portions of Tabernanthalog sorbate salt (50 mg, Experiment1-Sample A2, Form A) were dissolved in a binary solvent mixture composedof methanol (500 μl) and one of either water (250 μl, -A1), acetone (250μl, -B1), acetonitrile (250 μl, -C1), THF (250 μl, -D1) and DCM (250 μl,-E1).

Each vial was capped with aluminium foil, pierced, and allowed to standundisturbed until the evaporation is completed.

Equilibrium Humidity Stability (Experiment 10)

100 mg portions of Tabernanthalog sorbate salt (Experiment 1-Sample A2,Form A) were placed in the relevant vials. Experiment 10-Sample A wasopen-capped, and Experiment 10-Sample B was open-capped inside double,cable-tied, electrostatic polythene bags (to mimic a typical packagingconfiguration) and both were placed inside the same humidity chamber at95% RH at 20° C. The powders were finely divided and distributed evenlyover the base of the vial, such that equal material coverage across thepanel was observed. The samples were sub-sampled at intervals of t=0, 5d and 10 d and analysed by XRPD, DSC, TGA and ¹H NMR, for evidence ofphase change or chemical degradation

SC-XRD (Experiment 11) (Form A)

A crystalline sample of Experiment 11-Sample A1, which had beenrecrystallised from water, was isolated and submitted by Aptuit. A smallportion of this sample was suspended in perfluoroether oil and asuitable colourless block-shaped crystal with dimensions 0.24×0.07×0.03mm³ was selected. This crystal was mounted on a MITIGEN holder in oil ona Rigaku 007HF diffractometer with HF Varimax confocal mirrors, an UG2goniometer and HyPix 6000HE detector. The crystal was kept at a steadyT=100(2) K during data collection. The structure was solved with theShelXT 2014/5 (Sheldrick, 2014) solution program using dual methods andby using Olex2 1.5 (Dolomanov et al., 2009) as the graphical interface.The model was refined with ShelXL 2014/7 (Sheldrick, 2015) using fullmatrix least squares minimisation on F^(2.)

Experimental Reference: Experiment 12-Sample A2 (Hydrate)

To a vial containing Tabernanthalog sorbate salt (50 mg, Experiment1-Sample A2, Form A) was charged water (1.0 ml, 20.0 vol) and thecontents were heated from 20° C. to 70° C. at 0.5° C./min and was heldat that temperature for 1 h prior cooling down to 5° C. at 0.1° C./min.This experiment was a repeat of Experiment 12-A1, which was cooled downto 10° C. instead of 5° C. at the final step of the method. The methodwas programmed on a C16 apparatus. The contains of the vial remained atthat temperature for ca. 18 h before assessing their quality for SC-XRDanalysis by PLM.

A crystalline sample of Experiment 12-Sample A2, which had beenrecrystallised from water, was isolated and submitted by Aptuit. A smallportion of this sample was suspended in perfluoroether oil and asuitable colourless block-shaped crystal with dimensions 0.22×0.16×0.02mm³ was selected. This crystal was mounted on a MITIGEN holder in oil ona Rigaku 007HF diffractometer with HF Varimax confocal mirrors, a UG2goniometer and HyPix 6000HE detector. The crystal was kept at a steadyT=100(2) K during data collection. The structure was solved with theShelXT 2014/5 (Sheldrick, 2014) solution program using dual methods andby using Olex2 1.5 (Dolomanov et al., 2009) as the graphical interface.The model was refined with ShelXL 2014/7 (Sheldrick, 2015) using fullmatrix least squares minimisation on F^(2.)

G. Characterisation Data

1. Tabernanthalog Sorbate Salt (Experiment 13-Sample C1, Form aReference)

The characterization data are provided in FIGS. 741-756 and Table 289.

TABLE 289 Peak angle data of Experiment 13-Sample C1. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 5.7 15.54 100 11.4 7.76 4222.6 3.93 10 24.7 3.60 22

H. Experimental Data

1. Experiment 7-Sample A (Neat)

The characterization data are provided in FIGS. 757 and 758 .

2. Experiment 7-Sample B (water)

The characterization data are provided in FIGS. 759 and 760 .

3. Experiment 8-Sample A2

The characterization data are provided in FIGS. 761-765 and Table 290.

TABLE 290 Peak angle data of Experiment 8-Sample A2. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (º) d Value Rel. Intensity (%) 6.5 13.67 20 12.5 7.08 3812.8 6.90 20 13.6 6.48 23 15.4 5.74 12 17.6 5.03 18 17.9 4.94 53 18.14.89 100 18.7 4.73 52 20.1 4.42 61 20.6 4.32 22 21.8 4.07 81 25.0 3.5670 25.6 3.48 12 26.0 3.43 49 27.5 3.24 35 28.2 3.17 18 28.5 3.13 14 29.13.07 52 30.4 2.94 15 34.5 2.59 12

4. Experiment 8-Sample B

The characterization data are provided in FIGS. 766-769 and Table 291.

TABLE 291 Peak angle data of Experiment 8-Sample B2. Reported onlypeaks >10%. Rel. Intensity values calculated based on Net. Intensityvalues. 2-θ (°) d Value Rel. Intensity (%) 5.7 15.43 100 11.5 7.72 4718.8 4.71 11 23.0 3.86 12

5. Experiment 12-Sample A2

The characterization data are provided in FIG. 770 .

I. Supplementary Experiments

1. Evaporation Panel

Experiment 6

From methanol/acetone evaporation (Experiment B), the principalcomponent phase was Form A; small quantity of Pattern #1 was evident bypowder and small endo. by DSC (FIGS. 771-782 ). Likely the water ingresstook place during open evaporation.

Experiment 9-Sample A (Pattern #2)

Suspension equilibration in water (5 vol) at 20° C. for 7 days wasrepeated, aiming to obtain Pattern #2. Again, oven-drying was avoideddue to risk of conversion of the metastable form to Form A.

Analysis and isolation was the same as in Experiment 8.

XRPD diffractogram overlay of both wet (Experiment 9-Sample A1) and dry(Experiment 9-Sample A2) solid matched Pattern #2 (Experiment 3-SampleR1) (FIG. 783 ). Other characterization data are provided in FIGS. 784and 785 .

Experiment Reference: Experiment 9-Sample B

Characterization data are provided in FIGS. 786-789 .

Experiment Reference: Experiment 9-Sample C and D

Characterization data are provided in FIGS. 790 and 791 .

2. Stability Panel at 95% RH (Experiment 10)

Characterization data are provided in FIGS. 792-802 .

3. Re-Preparation of Tabernanthalog Sorbate Salt (Scale Up to 5 g)

Experiment 11-Sample A1

Characterization data are provided in FIGS. 803-807 .

4. Hypothetical Illustration of Hydration Classification

The hypothetical illustration of hydration classification is provided inScheme I.

5. DVS Analyses: 0% to 90% DVS Mass Per Unit Time Equilibrated at Dm/Dt(0.0002%/Min)

Experiment 1-Sample A2

Tabernanthalog sorbate salt; slightly hygroscopic up to 80% RH (redisotherm), hysteresis observed in the 80% to 50% RH range, held ontowater >50% RH, during the desorption cycle. Th., unary hydrate 5.0% w/w(20° C./95% RH, 5 days gave Pattern #2), likely seeing partialconversion into Pattern #2 and reversion back into Form A on thedesorption cycle (FIG. 808 ).

Residue at completion of the run was consistent with Form A (FIG. 809 ).

6. DSC Analyses, Form A

DSC data were collected from 25 to 220C at a scan rate of at 10° C.min⁻¹ (Table 292).

TABLE 292 Summary of results. melt onset peak Endset melt enthalpyExperiment ° C ° C. ° C. Jg-1 A1270-20-V2 143.89 148.83 151.95 −84.09Experiment 13-Sample 139.87 142.50 144.46 −105.78 C1 Experiment 1-SampleA2 140.03 142.50 144.06 −106.66 Experiment 6-Sample C1 144.66 148.83151.02 −100.48 Experiment 6-Sample D1 144.03 148.00 150.17 −166.35Experiment 6-Sample E1 145.00 148.83 151.59 −105.68 Experiment 7-SampleA 144.39 146.83 148.53 −122.47 neat Experiment 7-Sample B 144.54 146.83148.41 −115.11 water Experiment 8-Sample B2 141.82 144.33 145.97 −98.01Experiment 11-Sample 145.84 149.83 152.48 −92.27 A1 Mean 143.41 146.73148.86 −109.69 Variance 4.37 7.34 9.73 513.74

7. SC-XRPD

SC-XRPD Characterization of Tabernanthalog Sorbate Form A

Experimental. A crystalline sample of Experiment 11-Sample A1, which hadbeen recrystallised from water, was isolated and submitted by Aptuit. Asmall portion of this sample was suspended in perfluoroether oil and asuitable colourless block-shaped crystal with dimensions 0.24×0.07×0.03mm³ was selected. This crystal was mounted on a MITIGEN holder in oil ona Rigaku 007HF diffractometer with HF Varimax confocal mirrors, an UG2goniometer and HyPix 6000HE detector. The crystal was kept at a steadyT=100(2) K during data collection. The structure was solved with theShelXT 2014/5 (Sheldrick, 2014) solution program using dual methods andby using Olex2 1.5 (Dolomanov et al., 2009) as the graphical interface.The model was refined with ShelXL 2014/7 (Sheldrick, 2015) using fullmatrix least squares minimisation on F2.

Crystal Data. C20H2₆N2O₃, M_(r)=342.43, monoclinic, P2_(1/c) (No. 14),a=9.3410(3) Å, b=6.4173(2) Å, c=30.5108(12) Å, b=95.374(3°), a=g=90°,V=1820.90(11) Å³, T=100(2) K, Z=4, Z′=1, m(Cu K_(a))=0.675 mm⁻¹, 13832reflections measured, 3694 unique (R_(int)=0.0462) which were used inall calculations. The final wR₂ was 0.2098 (all data) and R_(I) was0.0826 (I≥2 s(I)).

Discussion A colourless block-shaped crystal with dimensions0.24×0.07×0.03 mm³ was mounted on a MITIGEN holder in oil. X-raydiffraction data were collected using a Rigaku 007HF diffractometer withHF Varimax confocal mirrors, an UG2 goniometer and HyPix 6000HE detectorequipped with an Oxford Cryosystems low-temperature device, operating atT=100(2) K.

Data were measured using profile data from w-scans of 0.5° per frame for1.5/6.0 s using Cu K_(a) radiation (Rotating anode, 40.0 kV, 30.0 mA).The total number of runs and images was based on the strategycalculation from the program CrysAlisPro 1.171.42.61a (Rigaku OD, 2022).The maximum resolution achieved was Q=76.7050.

Cell parameters were retrieved using the CrysAlisPro 1.171.42.61a(Rigaku OD, 2022) software and refined using CrysAlisPro 1.171.42.61a(Rigaku OD, 2022) on 5628 reflections, 41% of the observed reflections.Data reduction was performed using the CrysAlisPro 1.171.42.61a (RigakuOD, 2022) software which corrects for Lorentz polarisation. The finalcompleteness is 99.20% out to 76.705° in Q.

A multi-scan absorption correction was performed using CrysAlisPro1.171.42.61a (Rigaku Oxford Diffraction, 2022) Empirical absorptioncorrection using spherical harmonics, implemented in SCALE3 ABSPACKscaling algorithm. The absorption coefficient m of this material is0.675 mm-1 at this wavelength (I=1.54184 Å) and the minimum and maximumtransmissions are 0.768 and 1.000.

The structure was solved in the space group P2_(1/c) (#14) by using dualmethods using the ShelXT 2014/5 (Sheldrick, 2014) structure solutionprogram and refined by full matrix least squares minimisation on P usingversion 2014/7 of ShelXL 2014/7 (Sheldrick, 2015). All non-hydrogenatoms were refined anisotropically. The position of the N—H atoms H1 andH2 were located from the electron difference map and refined with theirthermal parameters linked to their parent atoms.

The positions of the remaining H atoms were calculated geometrically andrefined using the riding model (FIG. 810 and Table 293).

TABLE 293 SC-XRPD Characterization of Tabernanthalog Sorbate Form ACompound Experiment 11-Sample A1 Formula C₂₀H₂₆N₂O₃ D_(calc.)/g cm⁻³1.249 m/mm-1 0.675 Formula Weight 342.43 Colour colourless Shapeblock-shaped Size/mm³ 0.24 × 0.07 × 0.03 T/K    100(2) Crystal Systemmonoclinic Space Group P2₁/c a/Å  9.3410(3) b/Å  6.4173(2) c/Å30.5108(12) a/° 90 b/°  95.374(3) g/º 90 V/Å³ 1820.90(11) Z 4 Z′ 1Wavelength/Å 1.54184 Radiation type Cu K_(a) Q_(min)/° 4.755 Q_(max)/°76.705 Measured Refl's. 13832 Indep′t Refl′s 3694 Refl′s I ≥ 2 s(I) 3203R_(int) 0.0462 Parameters 300 Restraints 568 Largest Peak 0.359 DeepestHole −0.311 GooF 1.094 wR₂ (all data) 0.2098 wR₂ 0.2030 R₁ (all data)0.0931 R₁ 0.0826

The simulated powder diffraction pattern of Tabernanthalog·Sorbate (FormA) is provided in Table 293B

TABLE 293B Simulated powder diffraction pattern ofTabernanthalog•Sorbate (Form A). Rel Peak number 2-θ (º) Intensity %Peak #1 5.8 86 Peak #2 9.5 22 Peak #3 10.7 61 Peak #4 11.6 45 Peak #517.5 36 Peak #6 18.1 50 Peak #7 19.1 100 Peak #8 19.4 35 Peak #9 21.0 11Peak #10 21.7 43 Peak #11 22.3 10 Peak #12 22.9 53 Peak #13 23.4 10 Peak#14 24.7 47 Peak #15 25.0 96 Peak #16 25.6 22 Peak #17 27.3 38 Peak #1828.8 22 Peak #19 29.9 26

SC-XRPD Characterization of Tabernanthalog Sorbate Hydrate

Experimental. A crystalline sample of Experiment 12-Sample A2, which hadbeen recrystallised from water, was isolated and submitted by Aptuit. Asmall portion of this sample was suspended in perfluoroether oil and asuitable colourless block-shaped crystal with dimensions 0.22×0.16×0.02mm³ was selected. This crystal was mounted on a MITIGEN holder in oil ona Rigaku 007HF diffractometer with HF Varimax confocal mirrors, a UG2goniometer and HyPix 6000HE detector. The crystal was kept at a steadyT=100(2) K during data collection. The structure was solved with theShelXT 2014/5 (Sheldrick, 2014) solution program using dual methods andby using Olex2 1.5 (Dolomanov et al., 2009) as the graphical interface.The model was refined with ShelXL 2014/7 (Sheldrick, 2015) using fullmatrix least squares minimisation on F2.

Crystal Data. C20H28N₂O₄, M_(r)=360.44, monoclinic, P2_(1/c) (No. 14),a=16.07470(10) Å, b=12.14150(10) Å, c=10.85080(10) Å, b=109.2390(10°),a=g=900, V=1999.49(3) Å³, T-100(2) K, Z=4, Z′=1, m(Cu K_(a))=0.676 mm⁻¹,51305 reflections measured, 3786 unique (R_(int)=0.0483) which were usedin all calculations. The final wR₂ was 0.0874 (all data) and R_(I) was0.0347 (I≥2 s(I)).

Discussion X-ray data were collected upon a colourless block-shapedcrystal with dimensions 0.22×0.16×0.02 mm³, which was mounted on aMITIGEN holder in oil. X-ray diffraction data were collected using aRigaku 007HF diffractometer with HF Varimax confocal mirrors, a UG2goniometer and HyPix 6000HE detector equipped with an Oxford Cryosystemslow-temperature device, operating at T=100(2) K.

Data were measured using profile data from w-scans of 0.5° per frame for0.5/4.0 s using Cu K_(α) radiation (Rotating anode, 40.0 kV, 30.0 mA).The total number of runs and images was based on the strategycalculation from the program CrysAlisPro 1.171.42.61a (Rigaku OD, 2022).The maximum resolution achieved was Q=70.074°.

Cell parameters were retrieved using the CrysAlisPro 1.171.42.61a(Rigaku OD, 2022) software and refined using CrysAlisPro 1.171.42.61a(Rigaku OD, 2022) on 35970 reflections, 70% of the observed reflections.Data reduction was performed using the CrysAlisPro 1.171.42.61a (RigakuOD, 2022) software which corrects for Lorentz polarisation. The finalcompleteness is 100.00% (IUCr) out to 70.074° in Q.

A multi-scan absorption correction was performed using CrysAlisPro1.171.42.61a (Rigaku Oxford Diffraction, 2022) Empirical absorptioncorrection using spherical harmonics, implemented in SCALE3 ABSPACKscaling algorithm. The absorption coefficient m of this material is0.676 mm-1 at this wavelength (I=1.54184 Å) and the minimum and maximumtransmissions are 0.784 and 1.000.

The structure was solved in the space group P2_(1/c) (#14) by using dualmethods using the ShelXT 2014/5 (Sheldrick, 2014) structure solutionprogram and refined by full matrix least squares minimisation on F²using version 2014/7 of ShelXL 2014/7 (Sheldrick, 2015). Allnon-hydrogen atoms were refined anisotropically. The position of the N—Hatoms H1 and H2 and the O—H atoms H4A and H4B were located from theelectron difference map and refined with their thermal parameters linkedto their parent atoms. The positions of the remaining H atoms werecalculated geometrically and refined using the riding model.

There is a single molecule in the asymmetric unit, which is representedby the reported sum formula. In other words: Z is 4 and Z′ is 1. SC-XRPDCharacterization of Tabernanthalog Sorbate Hydrate is provided in Table294 and FIG. 811 .

TABLE 294 SC-XRPD Characterization of Tabernanthalog Sorbate HydrateCompound Experiment 12-Sample A2 Formula C₂₀H₂₈N₂O₄ D_(calc.)/g cm⁻³1.197 m/mm-1 0.676 Formula Weight 360.44 Colour colourless Shapeblock-shaped Size/mm³ 0.22 × 0.16 × 0.02 T/K     100(2) Crystal Systemmonoclinic Space Group P2₁/c a/Å 16.07470(10) b/Å 12.14150(10) c/Å10.85080(10) a/° 90 b/° 109.2390(10) g/º 90 V/Å3  1999.49(3) Z 4 Z′ 1Wavelength/Å 1.54184 Radiation type Cu Ka Q_(min)/° 2.912 Q_(max)/°70.074 Measured Refl′s. 51305 Indep′t Refl′s 3786 Refl′s I ≥ 2 s(I) 3542R_(int) 0.0483 Parameters 250 Restraints 0 Largest Peak 0.233 DeepestHole −0.188 GooF 1.039 wR₂ (all data) 0.0874 wR₂ 0.0861 R₁ (all data)0.0369 R₁ 0.0347

The simulated powder diffraction pattern of Tabernanthalog·Sorbate·H₂Ois provided in Table 294B

TABLE 294B Simulated powder diffraction pattern ofTabernanthalog•Sorbate•H₂O Rel Peak number 2-θ (º) Intensity % Peak #15.8 62 Peak #2 11.3 20 Peak #3 11.7 14 Peak #4 13.8 11 Peak #5 14.0 14Peak #6 17.0 32 Peak #7 17.4 18 Peak #8 17.9 25 Peak #9 18.7 28 Peak #1018.9 18 Peak #11 20.2 14 Peak #12 22.7 100 Peak #13 25.0 13 Peak #1427.7 11 Peak #15 28.1 11 Peak #16 30.0 22 Peak #17 32.3 14

Example 11: Preparation and Characterisation of Amorphous Forms ofTabernanthalog·Monofumarate and Tabernanthalog·Sorbate

Abbreviations φ_(i) Water activity coefficient a_(w) Water activity ASDAmorphous solid dispersion ca. circa (Latin: approximately) cf. Confer/conferatur (Latin: to confer, to compare) ° C. degree Celsius CPChemical Purity CP-MAS Cross Polarised Magic Angle Spinning (13C NMRsolid state technique) Da Dalton DSC Differential Scanning Calorimetry(measures changes in heat capacity) DTA Differential Thermal Analyses(measures changes in temperature) DVS Dynamic Vapour Sorption (usedinterchangeably with GVS) e.g. Exempli gratia (Latin: for example) etc.Et cetera (Latin: ′and others′ or ′and so on′) FT-IR FourierTransformed, InfraRed spectroscopy (prefixed mid and far) g Gram (s)GRAS Generally Recognised As Safe GVS Gravimetric Vapour Sorption h Hour(s) HFIPA Hexafluoroisopropanol HPLC High Performance LiquidChromatography HSM Hot Stage Microscopy (thermal microscopy) HUCDHeat-up / cool-down crystallisation i.e. Id Est (Latin: that is) IRInfraRed Spectroscopy J Joule Kelvin Kelvin. SI unit of temperature,used interchangeably with ° C. to express increment/ decrement oftemperature set point (e.g. ramp rate on DSC thermogram 10 K/min); noteK sign not prefixed by. KF Karl Fischer (determination of the watercontent by coulometric titration) kg Kilogram (s) LOD Loss On Drying magmagnification mAu milli-Absorption units (chromatographic unit of peakheight) m Au*s milli-Absorption units multiplied by second(chromatographic unit of peak area) MET/CR Aptuit chromatography methodreference min Minute (s) mg Milligram (s) ml Millilitre (s) mol mole,amount of substance N/A Not Applicable n.a. not analysed n.d. notdetected nm nanometre NMR Nuclear Magnetic Resonance oab on anhydrousbasis osfb on solvent free basis oasfb on anhydrous solvent free basispH −log [H+] or pH = −log a_(H) ⁺ pK_(a) −log (Ka), acid dissociationconstant pl isoelectric point, quoted in unit pH PLM Polarised LightMicroscopy RelRT Relative Retention Time (not be confused RT) REP/Aptuit report (REP) reference RFA Request For Analysis (unique referencenumber) RH Relative Humidity (aw * 100) RT Room Temperature (ambient,typically: 15 to 25° C.) S Second (s) SCXD Single Crystal X-RayDetermination SMPT Solvent mediated phase transition STA SimulatedThermal Analysis (STA = TGA + DTA) t time in seconds, minutes, hour,days etc. (interval specified in parentheses); alias in common use tonne(t) t Tonne, metric unit of mass (1000 kg; 1 Mg), (compaction force inkg, suffixed in parentheses) T Temperature recorded in degrees Celsius(° C.); alias in common use, SI unit of magnetic flux density, alsodenoted T MTBE Methyl tert-butyl ether TCNB2,3,5,6-Tetrachloronitrobenzene (C₆HCl₄NO₂, F.W. 260.89 gmol⁻¹) TFETrifluoroethanol (solvent used for solvent drop grinding) Tg Glasstemperature TGA Thermogravimetric Analysis th. theoretical UV UltraViolet vol. Volume or relative volume vs. versus v/v volume/volume WWatt w/w weight/weight XRPD X-Ray Powder Diffraction

Definitions Isostructural Crystals are said to be isostructural if theyhave the same crystal structure but not necessarily the same celldimensions nor the same chemical composition (Kalman, A., Parkanyi, L. &Argay, G. (1993) Acta Cryst. B49, 1039-1049.) Isomorphic two crystallinesolids are isomorphous if both have the same unit-cell dimensions andspace group (source, vide supra). Isomorphic desolvate via solventrelease from an isostructural solvate. Native Refers to an API in itsnative or non-ionised form. Normal light Light oscillating in alldirections perpendicular to the axis to which it travels. Particle sizeExpressed as a volume distribution, the range x10 > PSD < x90 capturesthe sizes of 80% of the particles. Plane polarised light Light passedthrough a polaroid filter which allows only light oscillating in oneplane to be transmitted. Polymorphism Crystalline solid able to exhibitdifferent crystalline phases. Photomicrograph Imaged captured of a smallobject under magnification through an optical microscope.Pseudopolymorphism Different crystal structure attributed to theincorporation of molecular water or solvent. Solvates Contains amolecule of solvent in the crystal lattice. Thermogram Differentialscanning calorimetry trace: heat flow on y-ordinate (mW), time(minutes)/temperature (° C.) on x-ordinate.

1. Summary

Characterisation of amorphous Tabernanthalog·Monofumarate andTabernanthalog·Sorbate:

-   -   Several attempts were made to generate amorphous forms of        Tabernanthalog·Monofumarate and Tabernanthalog·Sorbate utilising        methods such as lyophilisation/cryodesiccation, spray drying,        communition via bead milling and evaporation. None of the        methods were successful.    -   Thermal methods (TGA and DSC) were used to generate and analyse        the amorphous form in situ. The glass temperatures (Tg) were        determined for Tabernanthalog·Monofumarate and        Tabernanthalog·Sorbate.    -   Unable to proceed with large scale generation of amorphous        material, therefore, water activity studies were not progressed.    -   A unique powder pattern (#7) was observed after treatment of        Tabernanthalog·Sorbate with hexafluoroisopropanol (HFIPA).    -   Pattern #7 was regenerated by evaporation of a solution of        Tabernanthalog·Sorbate in HFIPA. The product was characterised        by ¹H NMR and ¹⁹F NMR spectroscopy, XRPD, DSC, TGA and underwent        stability to equilibrium humidity evaluations at 20° C./75% RH        and 40° C./75% RH.    -   Pattern #7 was determined to be        Tabernanthalog·Sorbate·HemiHFIPA, the solvate reverted to the        input form (Form A) by heating to 100° C., confirmed by XRPD        analysis.

2. Project Design

This report describes the following activities:

-   -   Analysis of the amorphous forms to determine their Tg.    -   Approaches taken to generate the amorphous forms, including        bead-milling, evaporation, nitrogen streams, and freeze        drying/cryodesiccation.    -   Amorphous forms were not generated utilising these techniques;        therefore, thermal treatments to access the amorphous phase were        carried out and in-situ analysis was performed. Employing a        thermocycle technique on both TGA and DSC to melt the sample and        then reanalyse to determine Tg, was successful for all        compounds.    -   Specimens of the Tabernanthalog salts were heated in XRPD low        background silicon sample holders to generate enough amorphous        material for XRPD analysis. Once the specimens were confirmed to        be amorphous, solution analyses by ¹HNMR and LCMS were used to        determine if thermal deterioration of the sample had occurred.

3 Results and Discussion 3.1 Tables of Characterisation

TABLE 295 Tabernanthalog•Sorbate Provenances of reference batchesTabernanthalog•Sorbate Experiment 1-Sample Reference batches: Experiment1-Sample D1, Experiment 1-Sample D1, Experiment 1- E1 Sample E1Molecular weight: 342.439 gmol⁻¹ Heated up past the melt Exact molecularweight: 342.19 event on a hot stage Molecular formula: C₂₀H₂₆N₂O₃microscope XRPD: Amorphous, (Experiment 1-Sample D1) ¹H NMR: (DMSO-d₆,400 MHz); δ 10.5 (s, 1H), 7.2 (d, J = 8.56 Hz, 1H), 7.1 (dd, J = 15.2,15.3 Hz, 1H), 6.7 (d, J=1.9 Hz, 1H), 6.6 (d, J = 8.56, 2.2 Hz, 1H), 6.2(d, m, 2H), 5.8 (d, J = 15.0 Hz, 1H), 3.7 (s, 3H), 2.8 (m, 2H), 2.7 (m,6H), 2.4 (s, 3H), 1.8 (d, J = 5.8 Hz, 3H) ppm; conforms to the molecularstructure (Σ25H)¹. (Experiment 1- Sample D1). ¹The molecular formula(C₂₀H₂₆N₂O₃) includes the carboxylic acid proton however, itco-resonates with water.

TABLE 296 Tabernanthalog•Sorbate•HemiHFIPA Provenances of referencebatches Tabernanthalog•Sorbate•HemiHFIPA Experiment 3-Sample Referencebatches: Experiment 3-Sample A2 A2 Molecular weight: 510.48 gmol⁻¹Crystallisation of Exact molecular weight: 510.20 Tabernanthalog•SorbateMolecular formula: C₂₃H₂₈F₆N₂O₄ from a solution of XRPD: 6.3º, 0.4º,13.3º, 14.0º, 15.4º, 15.8º, 16.1º, 16.5º, 17.1º Hexafluoroisopropanol17.1v, 17.7º, 19.0º, 19.4º, 21.2º, 21.9º, 22.6º, 23.3º, 23.8º, 25.1º,(HFIPA) 26.6º, 27.3º, 27.8º, 29.3º, 30.6º (2θ, 1 d.p), (Experiment3-Sample A2) DSC: onset 74.57° C. (−49.44 Jg⁻¹, endotherm, desolvation),102.81° C. (-41.07 Jg⁻¹, endotherm, desolvation), 143.78° C. (−8.17Jg⁻¹, endotherm, desolvation), (Experiment 3-Sample A2) TGA: onset70.03° C. (−12.4028% w/w, dehydration), 102.83° C. (−18.6893% w/w,dehydration), 220.77° C. (−55.2875% w/w, ablation) (Experiment 3-SampleA2. ¹H NMR: (DMSO-d₆, 400 MHz); δ 10.5 (s, 1H), 7.2 (d, 1H), 7.1 (dd,1H), 6.7 (d, 1H), 6.6 (dd, 1H), 6.2 (m, 2H), 5.8 (d, 1H), 3.7 (s, 3H),2.8 (t, 2H), 2.7 (d, 6H), 2.4 (s, 3H), 1.8 (d, 3H) ppm; conforms to themolecular structure (Σ25H). (Experiment 3-Sample A2) Q¹⁹F NMR: 13% w/wHFIPA (Experiment 3-Sample A2)

TABLE 297 Tabernanthalog•Monofumarate Provenances of reference batchesTabernanthalogMonofumarate Experiment 2-Sample Reference batches:Experiment 2-Sample D1, Experiment 2-Sample D1, Experiment 2- E1 SampleE1 Molecular weight: 346.383 gmol⁻¹ Heated up past the melt Exactmolecular weight: 346.153 event on a hot stage Molecular formula:C₁₃H₂₂N₂O₅ microscope XRPD: Amorphous (Experiment 2-Sample D1) ¹H NMR:(DMSO-d₆, 400 MHz); δ 10.6 (s, 1 H), 7.3 (d, 1 H), 6.8 (s, 1H), 6.6 (dd,1 H), 6.5 (s, 2 H), 3.7 (s, 3 H), 3.1 − 3.0 (m, 6 H), 2.9 (t, 2H), 2.6(s, 3 H) conforms to the molecular structure (Σ20H). (Experiment2-Sample D1)

FIGS. 812-875 provide additional details about the preparation andcharacterisation of amorphous forms of Tabernanthalog·Monofumarate andTabernanthalog·Sorbate.

3.2 Amorphous Study 3.2.1 Initial Studies to Generate Amorphous Studies

The purpose of this study was to generate amorphous material to becharacterized and used in water activity studies. To achieve this, thetwo salts were exposed to a variety of techniques in attempts togenerate the amorphous forms, including freeze drying, evaporation,vacuum desiccation and cryodesiccation spray drying. These techniqueswere not successful for the two salts Tabernanthalog·Monofumarate andTabernanthalog·Sorbate.

A new powder pattern (Pattern #7) was observed from experiments(Experiment 4-Sample B1) involving hexafluoroisopropanol treatments,indicating that a potential solvate was formed.

TABLE 299 Amorphous study of Tabernanthalog•Monofumarate andTabernanthalog•Sorbate. Experiment Scale Amorphisation Form byreferences Salt form investigation activity Outcome XRPD Experiment 4-Tabernanthalog•Sorbate  50 mg Freeze dry Crystalline Form A Sample A1Experiment 4- Tabernanthalog•Sorbate  50 mg Rotary Vac (MeOH)Crystalline Form A Sample A2 Experiment 4- Tabernanthalog•Sorbate  50 mgTHF/N₂ Crystalline Form A Sample A3 Experiment 4- Tabernanthalog•Sorbate 50 mg Antisolvent/N₂ Flow Crystalline Form A Sample A4 Experiment 4-Tabernanthalog•Sorbate  50 mg HFIP Evaporation Crystalline Pattern #7 Sample B1 Experiment 4- Tabernanthalog•Sorbate  50 mg HFIP EvaporationGum Sample B2 Experiment 4- Tabernanthalog•Sorbate  50 mg HFIPEvaporation Crystalline Pattern #7  Sample B3 Experiment 4-Tabernanthalog•Sorbate 100 mg Milling Crystalline Form A Sample C1Experiment 4- Tabernanthalog•Sorbate 100 mg Spray drying (MeOH)Crystalline Form A Sample D1 Experiment 4- Tabernanthalog•Sorbate 100 mgSpray drying (MeOH) Crystalline Form A Sample D2 Experiment 4-Tabernanthalog•Sorbate 100 mg Spray drying (15% Crystalline Form ASample E1 EtOH/Water) Experiment 5- Tabernanthalog•Monofumarate  50 mgFreeze dry Crystalline Pattern #1  Sample A1 Experiment 5-Tabernanthalog•Monofumarate  50 mg THF/N₂ Crystalline Pattern #11 SampleA2 Experiment 5- Tabernanthalog•Monofumarate  50 mg Crash coolCrystalline Pattern #3  Sample A3 Experiment 4- Tabernanthalog•Sorbate250 mg Hot Melt Extrusion Black Form A Sample D1 crystalline materialExperiment 4- Tabernanthalog•Sorbate 250 mg Hot Melt Extrusion BlackForm A Sample D2 (Overnight) crystalline material Experiment 6-Tabernanthalog•Sorbate  50 mg Milling Crystalline Form A Sample A1Experiment 6- Tabernanthalog•Sorbate  50 mg Milling Crystalline Form ASample A2 Experiment 6- Tabernanthalog•Sorbate  50 mg MillingCrystalline Form A Sample A3

3.2.2 Thermal Study

Initial experiments to produce the amorphous phase were unsuccessful forTabernanthalog·Sorbate and Tabernanthalog-Monofumarate. Therefore,thermal techniques would be used to access the amorphous phase in-situand complete characterisation of the glass temperature (Tg).

Each salt was analysed by DSC and TGA to determine the Tg of theamorphous form. Amorphous forms were generated by thermocycling the saltpast the melt temperature, cooling the sample, and once cooled thesamples were reheated. Open pan and sealed pan DSC were utilised, openpan DSC were heated past the melt event, cooled, and left to stand underambient conditions overnight.

Sealed pans were immediately cycled with no time left to stand.

TGA (open pan) samples were analysed by thermocycle, with no time forthe sample to stand under ambient conditions.

The amorphous forms were generated in these studies and characterisedwith their Tg being measured.

A hot stage microscope heating block was used to generate the amorphousphase in-situ, to allow analysis by XRPD. A silicon XRPD sample platewas loaded with the appropriate salt. The plate was heated past the meltevent, removed from the hot stage microscope block and cooled to ambientin air and analysed by XRPD to ensure that the amorphous form wasgenerated. The amorphous material was then analysed by ¹H NMR and LC-MSto ensure there was no change in chemical composition. Each sample wassuccessfully analysed obtaining the amorphous form and thermalcharacterisation, ¹H NMR and LC-MS proved there was no change inchemical composition of the samples after treatment.

TABLE 300 Thermal study of Tabernanthalog•Monofumarate andTabernanthalog•Sorbate. Experiment Temperature range references Saltform Experiment (° C.) Outcome Experiment 1- Tabernanthalog•Sorbate OpenPan DSC 20 to 165 to −20, O/N Amorphous Sample A1 20 to 230 Experiment1- Tabernanthalog•Sorbate Sealed DSC 20 to 165 to −20 to 230 AmorphousSample B1 Experiment 1- Tabernanthalog•Sorbate TGA 20 to 165 to −20 to230 Amorphous Sample C1 Experiment 1- Tabernanthalog•Sorbate Hot plateheat up 20 to 170 Amorphous Sample D1 Experiment 1-Tabernanthalog•Sorbate Experiment 1-Sample ambient Crystalline Sample D2D1 standing overnight Experiment 1- Tabernanthalog•Sorbate Hot stageplate heat up 20 to 170 Amorphous Sample E1 Experiment 2-Tabernanthalog•Monofumarate Open Pan DSC 20 to 210 to −20, O/N AmorphousSample A1 20 to 210 Experiment 2- Tabernanthalog•Monofumarate Sealed DSC20 to 210 to −20 to 210 Amorphous Sample B1 Experiment 2-Tabernanthalog•Monofumarate TGA 20 to 210 to −20 to 210 Amorphous SampleC1 Experiment 2- Tabernanthalog•Monofumarate Hot plate heat up 20 to 210Amorphous Sample D1 Experiment 2- Tabernanthalog•Monofumarate Hot stageplate heat up 20 to 210 Almost Amorphous Sample E1

TABLE 301 Glass transition temperature (Tg) forTabernanthalog•Monofumarate and Tabernanthalog•Sorbate. ExperimentalGlass temperature Reference Salt (Tgs) Experiment 1-Tabernanthalog•Sorbate 22° C. Sample B1 Experiment 2-Tabernanthalog•Monofumarate 63° C. Sample B1

3.2.3 Milling

Bead milling was attempted to generate the amorphous form ofTabernanthalog·Sorbate (Tabernanthalog·Sorbate, Form A). The saltunderwent neat milling and separately with the addition oftetradecafluorohexane (TDFH). The following experiments were performed:Experiment 6-Sample A1 (30 Hz, 2 h), Experiment 6-Sample A2 (30 Hz, 5.5h) and Experiment 6-Sample A3 (30 Hz 1 h, TDFH), the products from eachexperiment was analysed by XRPD to determine the extent of crystallinity(FIG. 812 ). None of the experiments provided amorphous material.

3.2.4 Generation of the Hexafluoroisopropanol (HFIPA) Solvate

During the initial amorphous experiments, a new powder pattern wasobserved attributed to a HFIPA solvate, this form was reprepared andcharacterised. (Section 7.1)

The Tabernanthalog·Sorbate·hemiHFIPA solvate was generated by theevaporation of a solution of Tabernanthalog·Sorbate(Tabernanthalog·Sorbate, Form A), dissolved in HFIPA. This wascharacterised by ¹H NMR, ¹⁹F NMR, XRPD, TGA, DSC.

Stability of the salt (Table 302) at elevated relative humidity wasexamined at 20 and 40° C., to determine if the HFIPA solvent can bereplaced by water to generate the isomorphic hydrate. A partial loss ofHFIPA was observed after 5 days, by ¹⁹F NMR. No change in the powderpattern was observed from this treatment and the powder pattern did notmatch the powder pattern of the hydrate single crystal structure.

Tabernanthalog·Sorbate-HemiHFIPA was heated to expel any solvent presentin the sample. The sample was analysed by XRPD to determine if the lossof solvent changed the form. The analysis demonstrated that upon loss ofsolvent, the phase reverts to Form A, the same as the input material(Tabernanthalog·Sorbate, FIG. 813 ).

TABLE 302 Generation of Tabernanthalog•Sorbate•hemiHFIPA Experimentreferences Input Activity Outcome Experiment 3- Tabernanthalog•SorbateHFIPA HemiHFIPA Sample A1 evaporation Experiment 3- Experiment 3-SampleA1 Drying HemiHFIPA Sample A2 under N2 Experiment 3- Experiment 3-SampleA2 75% RH 20° C. HemiHFIPA Sample B1 Experiment 3- Experiment 3-SampleA2 75% RH 40° C. HemiHFIPA Sample C1 Experiment 3- Experiment 3-SampleC1 TGA Converted to Sample C2 (20-100° C.) Form A

4. Conclusions

The preparation and characterisation of the amorphous phase was carriedout and Tg was determined for each compound (refer to Table 301). Theresidues were analysed by ¹H NMR spectroscopy and LC-MS, to confirm thatthe sample had not degraded during the thermal treatment.

Due to the issues associated with the generation of multiple grammequantities of the amorphous phase, the remainder of the change ordercould not be completed.

A Tabernanthalog·Sorbate hemiHFIPA solvate was generated from theevaporation of a solution of Tabernanthalog·Sorbate in HFIPA, theproduct was characterised by XRPD, ¹H NMR, ¹⁹F NMR, TGA and DSCanalyses. Stability of this sample was examined over 5 days at 75% RH at20 and 40° C. Samples, when reanalyzed, exhibited a reduction of HFIPAat the 5 days, time point and probable replacement of HFIPA by water inthe crystal structure.

5. Experimental 5.1 Instrumentation 5. 1.1 DSC

A Mettler Toledo DSC 3 instrument was used for the thermal analysisoperating with STARe™ software. The analysis was conducted in openaluminium pans (40 μl), under nitrogen and sample sizes ranged from 1 to10 mg. Typical analysis method was 20 to 250° C. at 10° C./minute.

Alternatively, a Mettler Toledo DSC1 with auto-sampler instrument wasused for the thermal analysis operating with STARe™ software. Theanalysis was conducted in open aluminium pans (40 μl), under nitrogenand sample sizes ranged from 1 to 10 mg. Typical analysis method was 25to 300° C. at 10 K/minute.

5.1.2 LC-MS

Routine Liquid Chromatography-Mass Spectrometry (LC-MS) data werecollected using the Agilent 1260 Infinity II interfaced with 1260Infinity II DAD HS and Agilent series 1260 Infinity II binary pump.

The instrument used a single quadrupole InfinityLab MSD. The instrumentwas calibrated up to 2000 Da.

LC-MS method parameters:

Inj.vol: 5 μl Detection: UV @ 254 nm Mobile Phase A: Acetonitrile+0.1%TFA/H₂O 95:5 Mobile Phase B: Acetonitrile+0.05% TFA/H₂O 5:95

Time (mins) % A % B 0.0 100 0 1 100 0 10.00 0 100 10.01 100 0 12.00 1000Flow Rate: 1.0 ml/minColumn temperature: 30° C.Run time 12 minutes.

5.1.3 ¹HNMR

¹H NMR spectra were acquired using a Bruker 400 MHz spectrometer anddata was processed using Topspin. Samples were prepared in DMSO-d₆ attypical concentrations of 10 to 20 mg/ml and up to 50 mg/ml forquantitative (Q)¹H NMR w/w assay and calibrated to the correspondingnon-deuterated solvent residual at 2.50 ppm.

5.1.4 ¹H NMR Assay

Assays (w/w) of the API by ¹H NMR spectroscopy were measured by theproject chemist using Topspin. Internal standard2,3,5,6-terachloronitrobenzene (TCNB, ca. 20 mg, F.W. 260.89) weredissolved in DMSO-d₆ (1.0 ml) and the ¹H NMR spectrum was acquired usingan extended relaxation method.

5.1.5 TGA

A Mettler Toledo TGA-2 instrument was used to measure the weight loss asa function of temperature from 25 to 500° C. The scan rate was typically5 or 10° C. per minute. Experiments and analysis were carried out usingthe STARe™ software. The analysis was conducted in 100 μl open aluminiumpans, under nitrogen and sample sizes ranged from 1 to 10 mg.

5.1.6 XRPD

X-ray powder diffraction (XRPD) analysis was carried out using a BrukerD2 Phaser powder diffractometer equipped with a LynxEye detector. Thespecimens underwent minimum preparation but, if necessary, were lightlymilled in a pestle and mortar before acquisition. The specimens werelocated at the centre of a silicon sample holder within a 5 mm pocket(ca. 5 to 10 mg). The samples were continuously spun during datacollection and scanned using a step size of 0.02°2-theta (2θ) betweenthe range of 4° to 40°2-theta or 5° to 60°2-theta. Data were acquiredusing either 9 minute or 20-minute acquisition methods. BrukerDiffrac.Suite was used to process the data

5.1.7 Bead Milling

Comminution was carried out by a MM500 Vario Mixing Mill, inside 1.5 and5 ml stainless steel jars with 5 mm ball bearings. Milling was performedat 30 Hz between 2-16 hours, sample sizes ranged from 50-100 mg. Theextent of pulverization was determined by the nature of the API, thenumber of ball bearings employed and the frequency of oscillation of thevessel.

5.1.8 Spray Drying

Spray drying was performed on a ProCept 4M8-Trix closed loop nitrogensystem, Nozzle size 1.0 mm. Parameters:

-   -   Inlet Gas Flow—0.3 ml/min    -   Inlet Temperature—130° C.    -   Column out temp—69° C.    -   Cyclone In Temperature—59° C.    -   Underpressure Column—5.5 mBar    -   Cyclone Differential Pressure—58 mBar    -   Nozzle Gas Flow—10.6 l/min    -   Chiller temp—−15° C.    -   Oxygen level—1.6%

5.2 General Procedures 5.2.1 Cryodesiccation/Freeze Drying

Experimental reference: Experiment 4-Sample A1, Experiment 5-Sample A1

Each salt was charged to a 7 ml vial (50 mg, 1.0 wt). To the vialcontaining Tabernanthalog·Monofumarate (Tabernanthalog·Monofumarate),was charged water (10.0 vol), to fully dissolve the sample.Tabernanthalog·Sorbate (A1270-076-A1) was taken-up in ethanol/water (15%v/v, 10 vol), a further charge of water (1.0 ml), was added to ensurethat the sample dissolved.

Vials containing the salt solutions were placed on the freeze drierapparatus overnight, and the cryo-desiccated products were recovered thefollowing morning and analysed by XRPD each product remainedcrystalline.

5.2.2 Evaporation Experimental Reference: Experiment 5-Sample A2

Tabernanthalog·Monofumarate (A1272−082-A2, 51.1 mg, 1.0 wt) was chargedto a 7 ml scintillation vial followed by THE (2 ml, 60 vol), thesuspension was heated to 50° C., until full dissolution was observed.The vial was stoppered by foil and a pin hole was pierced in the top.The vial was located under a steady N₂ stream. The solvent evaporated todryness overnight, and the product was analysed by XRPD yieldingcrystalline material

5.2.3 fIPA Evaporation

Experimental Reference: Experiment 3-Sample A1, Experiment 3-Sample A2

Tabernanthalog·Sorbate (A1270−076-A1, 99.4 mg, 1.0 wt) was charged to a7 ml scintillation vial, followed by hexafluoroisopropanol (HFIPA, 5.0vol, 0.5 ml), after which, the sample fully dissolved. The cap wasreplaced by foil and pierced on the top. Solvent was allowed toevaporate, to afford a dry, brown solid that was analysed by XRPDyielding crystalline pattern #7. Sample were dried under N2 stream for 5h and reanalysed by XRPD, remaining as pattern #7

5.2.4 Rotary Evaporation Experimental Reference: Experiment 4-Sample B1

Tabernanthalog·Sorbate (A1270−076-A1, 50.0 mg, 1.0 wt) was charged to a7 ml scintillation vial followed by hexafluoroisopropanol (HFIPA, 0.5ml, 10 vol), to yield a clear solution. The solution was concentrated todryness, by rotary evaporation, yielding an oil, that was allowed tostand undisturbed overnight. The product exhibited crystallinity byXRPD.

5.2.5 Binary Solvent

Experimental reference: Experiment 4-Sample A4

Tabernanthalog·Sorbate (A1270−076-A1, 50.0 mg, 1.0 wt) was charged to a7 ml scintillation vial, followed by methanol (300 μl, 6.0 vol). Thesolution was clarified by filtration into a 7 ml scintillation vial,containing diethyl ether (1.0 ml, 20.0 vol). The solution was driedunder sustained N₂ stream and was analysed by XRPD yielding crystallinematerial HFIPA desiccator sample Experimental reference: Experiment4-Sample B2, Experiment 4-Sample B3 Tabernanthalog·Sorbate (Experiment4-Sample B1, 50.0 mg, 1.0 wt, Pattern #7) was taken up in HFIPA (50.0 l,1 vol) and transferred to a low background, silicon XRPD sample plate,and dried inside a vacuum desiccator for 4 h at 20° C. The sample wasremoved from the desiccator to yield a clear gum, that was analysed byXRPD yielding partially crystalline material. Sample placed intodesiccator and left to dry overnight before reanalysis by XRPD yieldingfully crystalline material indicating crystallisation of sampleovernight.

5.2.6 Spray Drying Experimental Reference: Experiment 4-Sample D1

Tabernanthalog·Sorbate (A1270−076-A1, 102 mg, 1 wt) was charged to a 7.0ml scintillation vial followed by methanol (1.9 ml, 19.0 vol). Thesolution was loaded into the spray drier apparatus.

The procedure yielded a brown powder (30 mg, 30% th.). Crystallinematerial was evident by XRPD. The specimen was allowed to stand,undisturbed overnight, prior to reanalysis by XRPD; consequently, thespecimen exhibited much improved crystallinity, after this time.

5.2.7 Bead Milling Experimental Reference: A1270-084-A1

Tabernanthalog·Sorbate (A1270-076-A1, Form A) was charged to a 1.5 mlsteel milling-vessel with a single 5 mm ball bearing. The sample wasmilled for 5.5 h at 30 Hz and yielded an off-white powder, that wasanalysed by XRPD, no change in crystallinity.

5.2.8 DSC Experimental Reference: Experiment 1-Sample A1, Experiment1-Sample B1, Experiment 2-Sample A1, Experiment 2-Sample B1

Two DSC pans were charge with the appropriate salt(Tabernanthalog·Sorbate, A1270−076-A1 and Tabernanthalog·Monofumarate,Tabernanthalog·Monofumarate), the first DSC pan was not sealed (open panDSC), the second was sealed (hermetic sealed pan DSC). The open pan DSCwas cycled from 20° C. to just after the melt event for each, cooled to−20° C. and left to stand under ambient conditions over night. The openpan DSC was then heated to just before the thermal degradation event(Tabernanthalog·Sorbate ca. 160° C., Tabernanthalog·Monofumarate ca.210° C.) The hermetic sealed DSC was heated from 20° C. to just afterthe melt event, cooled to −20° C. then headed to just before the samedegradation event.

5.2.9 TGA Experimental Reference: Experiment 1-Sample C1, Experiment2-Sample C1

Two TGA crucibles were charged with the appropriate salt(Tabemanthalog·Sorbate, A1270-076-A1, Tabernanthalog·Monofumarate,Tabernanthalog·Monofumarate), both were thermocycled from 20° C. to pastthe melt event and then cooled to −20° C., each pan was then immediatelyheated to just before the degradation event to measure the Tg event.

5.2.10 Hot Plate Melt Experimental Reference: Experiment 1-Sample D1,Experiment 2-Sample E1

A XRPD, low-background silicon sample plate was loaded with theappropriate salt (Tabernanthalog·Sorbate, Tabernanthalog·Monofumarate),and heated on a hot plate mantle until melted, the melt was cooled andanalysed by XRPD to ensure amorphous.

5.2.11 Hot Stage Microscope Melt Experimental Reference: Experiment1-Sample E1, Experiment 2-Sample E1,

A XRPD, low background silicon sample plate was loaded with theappropriate salt (Tabernanthalog·Sorbate, Tabernanthalog·Monofumarate,)and heated on a hot stage microscope block until melted; the specimenswere cooled and analysed by XRPD to ensure that the phases wereamorphous. Once amorphous material was obtained, both samples wereanalysed by LC-MS and ¹H NMR to ensure that no change in chemicalcomposition had occurred.

5.2.12 Stability at 75% RH 20° C. and 40° C.

Experimental reference: Experiment 3-Sample B1, Experiment 3-Sample C1Tabernanthalog·Sorbate·HemiHFIPA (Experiment 3-Sample A2, 28.2 mg, 1 wt)was charged into a wide necked solid sample vial, the uncapped vial wasplaced inside a larger amber jar containing an aqueous NaCl slurry. Theamber jar was sealed and left to stand for 5 days. The specimen analysedby XRPD, ¹⁹F NMR, TGA and DSC after 5 days. No change in powder patternobserved and a small decrease in HFIPA content after 5 days,

TABLE 303 Peak angle data of Experiment 3-Sample A2. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 22.6 3.9 100.0 9.4 9.4 79.617.7 5.0 63.4 17.1 5.2 59.4 19.0 4.7 54.6 6.3 14.0 51.4 15.4 5.8 44.717.1 5.2 40.3 19.4 4.6 33.5 13.3 6.7 30.3 23.8 3.7 30.2 23.3 3.8 30.121.2 4.2 29.3 16.1 5.5 26.8 15.8 5.6 23.1 27.3 3.3 22.0 21.9 4.1 15.230.6 2.9 13.5 27.8 3.2 12.7 16.5 5.4 12.3 14.0 6.3 12.2 25.1 3.6 12.126.6 3.4 11.5 29.3 3.0 10.8

TABLE 304 Peak angle data of Experiment 4-Sample A1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 5.7 15.6 5 100.0 11.4 7.829.9 18.9 4.7 15.9 22.6 3.9 11.9 24.5 3.6 17.1 24.6 3.6 19.9

TABLE 305 Peak angle data of Experiment 4-Sample A2. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 5.6 15.64 100.0 11.3 7.8040.0 18.9 4.69 13.6

TABLE 306 Peak angle data of Experiment 4-Sample A3. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 5.7 15.51 100 10.5 8.39 1811.4 7.75 45 18.0 4.93 13 18.9 4.69 27 19.2 4.62 11 21.4 4.15 11 22.73.92 14 24.4 3.64 11 24.7 3.60 23

TABLE 307 Peak angle data of Experiment 4-Sample A4. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 5.7 15.59 100 11.4 7.78 4818.9 4.70 19 22.8 3.89 11

TABLE 308 Peak angle data of Experiment 4-Sample B1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 5.7 15.53 100 11.4 7.77 23

TABLE 309 Peak angle data of Experiment 4-Sample B3. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 22.5 3.95 100 22.7 3.92 997.6 11.61 98 5.7 15.38 67 22.6 3.94 58 17.1 5.20 48 13.3 6.66 38 15.45.75 38 9.5 9.34 33 11.5 7.72 30 23.3 3.81 27 19.0 4.68 25 17.2 5.14 1923.6 3.76 19 14.1 6.29 18 23.8 3.74 18 15.2 5.81 5 16 17.7 5.01 14 6.314.02 14 15.9 5.56 13 23.1 3.85 12 16.9 5.24 12 21.3 4.17 12 17.5 5.0511

TABLE 310 Peak angle data of Experiment 4-Sample C1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 5.7 15.57 100 18.9 4.70 8724.7 3.61 76 11.4 7.75 56 24.5 3.63 52 10.5 8.43 50 22.6 3.93 45 19.14.64 44 17.9 4.94 36 21.4 4.15 30 26.9 3.31 22 17.3 5.12 22 9.4 9.42 1829.6 3.02 16 28.5 3.13 16 25.2 3.53 13

TABLE 311 Peak angle data of Experiment 4-Sample D1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 18.9 4.68 100 5.7 15.36 2710.5 8.41 24 15.1 5.85 22 27.4 3.25 22 18.0 4.93 17 24.7 3.60 12

TABLE 312 Peak angle data of Experiment 4-Sample D2. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (°) d Value (%) 5.7 15.46 100 18.9 4.69 5510.5 8.39 47 11.5 7.72 38 24.7 3.60 35 18.0 4.92 27 24.6 3.62 24 19.24.63 24 18.4 4.81 23 22.7 3.92 20 10.3 8.57 18 9.4 9.36 18 21.5 4.14 1517.4 5.09 14 26.9 3.31 10

TABLE 313 Peak angle data of Experiment 4-Sample E1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 18.9 4.68 100 5.7 15.57 7724.7 3.61 49 19.1 4.63 46 10.5 8.39 44 18.4 4.82 42 18.0 4.91 40 11.47.77 32 24.5 3.64 31 22.6 3.92 29 10.4 8.49 28 21.5 4.14 27 17.5 5.08 2226.8 3.32 15 9.5 9.35 14 15.2 5.84 11 27.4 3.25 11

TABLE 314 Peak angle data of Experiment 5-Sample A1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 16.3 5.43 100 9.1 9.76 9125.6 3.48 81 19.3 4.60 31 26.8 3.33 31 25.1 3.54 22 16.7 5.31 20 18.14.89 19 22.3 3.99 16 27.2 3.27 15 30.0 2.98 14 23.1 3.85 11

TABLE 315 Peak angle data of Experiment 5-Sample A2. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 7.4 11.89 100.0 21.5 4.1336.2 16.0 5.54 34.1 20.3 4.38 15.9 25.7 3.46 11.5 20.8 4.27 10.1

TABLE 316 Peak angle data of Experiment 5-Sample A3. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 8.2 10.75 100 11.2 7.88 3117.1 5.20 29 24.4 3.65 13 23.8 3.74 13 21.5 4.12 13 20.2 4.39 12 8.99.93 11

TABLE 317 Peak angle data of Experiment 6-Sample A1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 18.9 4.70 100 24.5 3.63 6717.9 4.94 45 22.6 3.94 37 5.6 15.77 35 17.4 5.10 32 11.3 7.82 29 10.58.42 28 21.4 4.15 27 26.7 3.34 20 25.3 3.52 18 26.8 3.33 16 29.6 3.02 149.4 9.44 14 19.7 4.51 13 28.5 3.13 13

TABLE 318 Peak angle data of Experiment 6-Sample A2. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 18.9 4.70 100 24.6 3.62 8424.5 3.63 69 19.1 4.65 53 17.9 4.94 52 22.6 3.93 49 5.6 15.70 49 21.44.15 39 10.5 8.42 38 11.4 7.79 33 17.3 5.11 33 26.8 3.32 25 29.6 3.02 2028.5 3.13 20 25.3 3.52 20 9.4 9.42 16 19.7 4.50 15 22.0 4.04 12

TABLE 319 Peak angle data of Experiment 6-Sample A3. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 18.9 4.70 100 5.7 15.54 9224.7 3.61 80 24.5 3.62 57 10.5 8.42 53 11.4 7.75 52 22.6 3.93 52 17.94.94 45 19.1 4.63 44 21.4 4.15 37 17.4 5.11 32 26.9 3.32 25 9.4 9.41 2428.5 3.13 19 29.6 3.01 19 25.3 3.52 16 22.1 4.03 14 20.8 4.27 11 19.74.49 10

TABLE 320 Peak angle data of Experiment 1-Sample D2. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 18.7 4.73 100 24.5 3.62 9422.5 3.95 62 11.2 7.86 61 24.2 3.67 55 22.8 3.90 46 19.0 4.66 45 21.34.17 36 17.9 4.96 36 26.7 3.33 33 18.2 4.86 32 28.4 3.14 25 29.5 3.02 2521.9 4.05 19 17.2 5.14 17 20.6 4.30 14 25.2 3.53 13 29.1 3.06 12 10.38.57 11 23.4 3.80 11 27.3 3.27 11

TABLE 321 Peak angle data of Experiment 2-Sample E1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 19.4 4.57 100 26.0 3.43 7517.0 5.21 29 12.9 6.87 28 24.5 3.63 18 20.6 4.31 16 18.0 4.93 16 15.65.69 15

TABLE 322 Peak angle data of Experiment 3-Sample A1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 9.4 9.36 100 6.3 14.04 5819.0 4.68 48 22.6 3.93 23 17.7 5.02 19 17.1 5.20 16 15.8 5.61 16 19.44.57 15 15.4 5.75 14 17.2 5.15 13 25.4 3.51 11

TABLE 323 Peak angle data of Experiment 3-Sample B1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 9.5 9.30 100 19.0 4.66 7922.6 3.92 73 6.4 13.90 60 15.4 5.74 59 17.7 5.01 57 17.1 5.18 49 17.25.14 46 19.5 4.56 44 13.3 6.66 43 15.9 5.58 30 21.3 4.17 27 23.8 3.73 2716.1 5.49 26 23.3 3.81 23 21.9 4.05 23 27.3 3.26 20 25.4 3.50 19 14.16.29 19 25.1 3.54 12 26.6 3.35 11

TABLE 324 Peak angle data of Experiment 3-Sample C1. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 22.7 3.92 100 17.7 5.00 5917.2 5.17 57 9.5 9.29 56 19.0 4.66 49 15.4 5.73 46 13.3 6.65 44 6.313.91 35 19.5 4.55 33 16.2 5.48 31 23.8 3.73 28 23.4 3.81 26 21.3 4.1624 16.0 5.54 22 27.3 3.26 20 21.9 4.05 16 14.1 6.28 15 25.1 3.54 13 16.65.35 13 27.9 3.20 12 26.6 3.35 12 25.5 3.49 12 30.7 2.91 11

TABLE 325 Peak angle data of Experiment 3-Sample C2. Reported onlypeaks > 10%. Rel. Intensity values calculated using Net Intensityvalues. Rel. Intensity 2-θ (º) d Value (%) 5.7 15.49 100 18.9 4.69 9031.7 2.82 89 24.7 3.60 80 10.5 8.39 53 18.0 4.93 53 22.7 3.92 53 11.47.73 50 19.2 4.61 45 21.4 4.14 44 24.5 3.64 40 17.4 5.10 32 26.9 3.31 279.4 9.36 20 28.5 3.13 17 25.3 3.51 17 22.1 4.02 15 29.7 3.01 15 20.84.26 13 19.8 4.48 10

SC-XRD Bond Length Comparison

Intermolecular interactions of the single crystal structures obtainedwere analysed. Bond length of interactions at the salification siteswere ˜5% shorter on average than hydrogen bonding interactions at otheravailable sites, suggesting these are salts (incorporation of ionisedspecies into the crystal network) being formed and not co-crystals(incorporation of neutral species into the crystal network).

TABLE 326 Intermolecular bonds observed in Crystal structures.Salification Hydrogen Hydrogen bond bond bond Experiment length lengthlength references Salt form (A) (A) (A) A1270- Tabernanthalog• 2.70152.847 — 076-A1 Sorbate A1272- Tabernanthalog• 2.704 2.893 2.477 032-M2Monofumarate (between Fumarates) A1272- Tabernanthalog• 2.697 2.811032-M2 Monofumarate

NMR Shift Comparison

Comparison of ¹H NMR spectrum between the native form of Tabernanthalogcompared to Tabernanthalog·Sorbate and Tabernanthalog·Monofumarate,Small shift in ppm between peaks near the ionisation sites, howevershifts appear to be driven by ΔpK_(a.)

¹H NMR Spectrum Used:

-   -   Tabernanthalog·Native    -   Tabernanthalog·Sorbate    -   Tabernanthalog·Monofumarate

TABLE 327 ¹H NMR peak shift comparison, reported in ppm. Tabern- Tabern-Tabern- anthalog• anthalog• anthalog• Proton Native Sorbate ΔsorbateMonofumarate Δfumarate A 2.392 2.405 0.013 2.595 0.203 BCDI 2.715 2.7360.021 2.97 0.255 BCDI 2.858 2.856 −0.002 2.996 0.138 Average 0.01 0.20

LCMS

LC-MS was performed on each salt (Tabernanthalog·Sorbate,Tabernanthalog·Monofumarate,) to ensure there was no change in chemicalcomposition during the heating process, two peaks were observed inA1270-088-E1, switching in intensity with changing UV wavelength. Asample was pure sorbic acid was also analysed to ensure the 2^(nd) peak(2.65 min) was sorbic acid. The sample of pure sorbic acid contained asingular peak (2.61 min) suggesting the first peak is in fact API, thesecond sorbic acid.

In view of the many possible embodiments to which the principles of thedisclosed invention may be applied, it should be recognized that theillustrated embodiments are only preferred examples of the invention andshould not be taken as limiting the scope of the invention. Rather, thescope of the invention is defined by the following claims. We thereforeclaim as our invention all that comes within the scope and spirit ofthese claims.

1.-71. (canceled)
 72. A tabernanthalog salt or solid form.
 73. Thetabernanthalog salt of claim 72, wherein the salt is crystalline. 74.The tabernanthalog salt of claim 72, wherein the salt is amorphous. 75.The tabernanthalog salt of claim 72, wherein the salt is formed from anacid selected from galactaric (mucic) acid, naphthalene-1,5-disulfonicacid, citric acid, sulfuric acid, d-glucuronic acid,ethane-1,2-disulfonic acid, lactobionic acid, p-toluenesulfonic acid,D-glucoheptonic acid, thiocyanic acid, L-pyroglutamic acid,methanesulfonic acid, L-malic acid, dodecylsulfuric acid, hippuric acid,naphthalene-2-sulfonic acid, D-gluconic acid, benzenesulfonic acid,D,L-lactic acid, oxalic acid, oleic acid, glycerophosphoric acid,succinic acid, isethionic acid, glutaric acid, L-aspartic acid, cinnamicacid, maleic acid, adipic acid, phosphoric acid, sebacic acid,ethanesulfonic acid, (+)-camphoric acid, glutamic acid, acetic acid, ora combination thereof.
 76. The tabernanthalog salt of claim 72, whereinthe salt is a fumarate, monofumarate salt or hemi-fumarate salt.
 77. Thetabernanthalog salt of claim 72, wherein the salt is a fumarate saltwith a crystalline polymorphic form having Pattern #1, Pattern #2a (FormB), Pattern #2b, Pattern #2c, Pattern #2d, Pattern #3, Pattern #4a,Pattern #4b, Pattern #5, Pattern #6a (Form A), Pattern #6b, Pattern #7,Pattern #8, Pattern #9, Pattern #10, Pattern #11, Pattern #12, Pattern#13, Pattern #14 (Form I), Pattern #15, Pattern #16, Pattern #17,Pattern #18, Pattern #19, Pattern #20, Pattern #21, Pattern #22, or amixture thereof.
 78. The tabernanthalog salt of claim 76, wherein thesalt is a crystalline polymorphic form of tabernanthalog monofumaratesalt having Pattern #6a (Form A).
 79. The tabernanthalog salt of claim76, wherein the salt is a crystalline polymorphic form of tabernanthalogmonofumarate salt having Pattern #2a (Form B).
 80. The tabernanthalogsalt of claim 76, wherein the salt is a crystalline polymorphic form oftabernanthalog hemifumarate having Pattern #14 (Form I).
 81. Thetabernanthalog salt of claim 72, wherein the salt is an acid additionsalt.
 82. The tabernanthalog salt of claim 72, wherein the salt is asorbate.
 83. The tabernanthalog salt of claim 72, wherein the salt is atartrate salt.
 84. The tabernanthalog salt of claim 72, wherein the saltis a malate salt.
 85. The tabernanthalog salt of claim 72, wherein thesalt is a tosylate salt.
 86. The tabernanthalog salt of claim 72,wherein the salt is a benzoate salt.
 87. The tabernanthalog salt ofclaim 72, wherein the salt is an adipate salt.
 88. The tabernanthalogsalt of claim 72, wherein the salt is a glucoronate salt.
 89. Thetabernanthalog salt of claim 72, wherein the salt is a phosphate salt.90. The tabernanthalog salt of claim 72, wherein the salt is anedisylate salt.
 91. The tabernanthalog salt of claim 72, wherein thesalt is a sulfate salt.
 92. The tabernanthalog salt of claim 72, whereinthe salt is a maleate salt.
 93. The tabernanthalog salt of claim 72,wherein the salt is a galactarate salt.
 94. The tabernanthalog salt ofclaim 72, wherein the salt is a citrate salt.
 95. The tabernanthalogsalt of claim 72, wherein the salt is a glycolate salt.
 96. Thetabernanthalog salt of claim 72, wherein the salt is a succinate salt.97. The solid form of claim 72, wherein the solid form is a free baseform of tabernanthalog.
 98. A pharmaceutical composition comprising thetabernanthalog salt or solid form of claim 72 and a pharmaceuticallyacceptable excipient.
 99. A method for treating a disease or disorder ina subject in need thereof, comprising administering to the subject thetabernanthalog salt or solid form of claim 72.